Compound for organic electronic element, organic electronic element using the same, and electronic device thereof

ABSTRACT

The present invention provides a novel compound which is capable of improving light-emitting efficiency, stability and lifespan of an element, an organic electronic element using the same, and an electronic device thereof.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is a continuation of U.S. patent application Ser. No.15/822,897, filed on Nov. 27, 2017, which is a continuation of U.S.patent application Ser. No. 14/654,917, filed on Sep. 15, 2015, which isa 371 U.S. National Stage of International Application No.PCT/KR2013/010680, filed on Nov. 22, 2013. This application also claimspriority to Korean Application No. 10-2012-0152002, filed on Dec. 24,2012. The entire disclosures of the above applications are incorporatedherein by reference.

TECHNICAL FIELD

The present invention relates to a compound for an organic electronicelement, an organic electronic element using the same, and an electronicdevice thereof.

BACKGROUND ART

In general, an organic light emitting phenomenon refers to a phenomenonin which electronic energy is converted into light energy by means of anorganic material. An organic electronic element utilizing the organiclight emitting phenomenon usually has a structure including an anode, acathode, and an organic material layer interposed therebetween. Here, inmany cases, the organic material layer may have a multilayered structureincluding multiple layers made of different materials in order toimprove the efficiency and stability of an organic electronic element,and for example, may include a hole injection layer, a hole transportlayer, a light emitting layer, an electron transport layer, an electroninjection layer, and the like.

A material used as an organic material layer in an organic electronicelement may be classified into a light emitting material and a chargetransport material, for example, a hole injection material, a holetransport material, an electron transport material, an electroninjection material, and the like according to its function.

It is required to develop a hole injection layer material that retardspenetration/diffusion of metal oxides from an anode electrode (ITO) intoan organic layer, which is one cause for the shortened lifetime of anorganic electronic element, and has stability against Joule heatgenerated during the operation of an organic electronic element, thatis, a high glass transition temperature. Also, it has been reported thata low glass transition temperature of a hole transport layer materialhas a great effect on the lifetime of an organic electronic elementbecause the uniformity of a thin film surface collapses during theoperation of the element. In general, deposition is a main method offorming an OLED, and thus there is an actual need to develop a materialthat is durable to such a deposition method, that is, a highlyheat-resistant material.

That is, in order to allow an organic electronic element to fullyexhibit the above-mentioned excellent features, it should beprerequisite to support a material constituting an organic materiallayer in the element, for example, a hole injection material, a holetransport material, a light emitting material, an electron transportmaterial, an electron injection material, or the like, by a stable andefficient material. However, such a stable and efficient organicmaterial layer material for an organic electronic element has not yetbeen fully developed. Accordingly, there is a continuous need to developnew materials for an organic material layer.

DETAILED DESCRIPTION OF THE INVENTION Technical Problem

In order to solve the above-mentioned problems occurring in the priorart, an object of the present invention is to provide a compound thatallows an organic electronic element to have high luminous efficiency,low driving voltage, and high heat resistance and to be improved incolor purity and lifetime, an organic electronic element using the same,and an electronic device thereof.

Technical Solution

In accordance with an aspect of the present invention, there is provideda compound represented by Formula 1 below.

In another aspect of the present invention, there are provided anorganic electronic element using the compound represented by the aboveformula and an electronic device.

Advantageous Effects

The inventive compound allows an organic electronic element to not onlyhave high luminous efficiency, low driving voltage, and high heatresistance, but also be significantly improved in color purity andlifetime.

BRIEF DESCRIPTION OF THE DRAWING

The FIGURE illustrates an example of an organic light emitting diodeaccording to an embodiment of the present invention.

MODE FOR CARRYING OUT THE INVENTION

Hereinafter, some embodiments of the present invention will be describedin detail with reference to the accompanying illustrative drawings.

In designation of reference numerals to components in respectivedrawings, it should be noted that the same elements will be designatedby the same reference numerals although they are shown in differentdrawings. Further, in the following description of the presentinvention, a detailed description of known functions and configurationsincorporated herein will be omitted when it may make the subject matterof the present invention rather unclear.

In addition, terms, such as first, second, A, B, (a), (b) or the likemay be used herein when describing components of the present invention.Each of these terminologies is not used to define an essence, order orsequence of a corresponding component but used merely to distinguish thecorresponding component from other component(s). It should be noted thatif it is described in the specification that one component is“connected,” “coupled” or “joined” to another component, a thirdcomponent may be “connected,” “coupled,” and “joined” between the firstand second components, although the first component may be directlyconnected, coupled or joined to the second component.

Unless otherwise stated, the term “halo” or “halogen” as used hereinincludes fluorine, chlorine, bromine, and iodine.

Unless otherwise stated, the term “alkyl” or “alkyl group” as usedherein has, but not limited to, 1 to 60 carbon atoms.

Unless otherwise stated, the term “alkenyl” or “alkynyl” as used hereinhas, but not limited to, double or triple bonds of 2 to 60 carbon atoms.

Unless otherwise stated, the term “cycloalkyl” as used herein means, butnot limited to, alkyl forming a ring having 3 to 60 carbon atoms.

Unless otherwise stated, the term “alkoxy group” as used herein has, butnot limited to, 1 to 60 carbon atoms.

Unless otherwise stated, the term “aryl group” or “arylene group” asused herein has, but not limited to, 6 to 60 carbon atoms.

Herein, the aryl group or arylene group means a homocyclic orheterocyclic aromatic group, and includes an aromatic ring that isformed in conjunction with an adjacent substituent linked thereto orparticipating in the reaction. Examples of the aryl group may include aphenyl group, a biphenyl group, a fluorine group, and a spirofluorenegroup.

Unless otherwise stated, the term “heteroalkyl” as used herein meansalkyl containing one or more heteroatoms. Unless otherwise stated, theterm “heteroaryl group” or “heteroarylene group” as used herein means,but not limited to, a C₃ to C₆₀ aryl or arylene group containing one ormore heteroatoms, includes both homocyclic and heterocyclic rings, andmay also be formed in conjunction with an adjacent group.

Unless otherwise stated, the term “heterocyclic alkyl” or “heterocyclicgroup” as used herein contains one or more heteroatoms, has 2 to 60carbon atoms, includes both homocyclic and heterocyclic rings, and mayalso be formed in conjunction with an adjacent group. Also, theheterocyclic group may mean an alicyclic and/or aromatic groupcontaining heteroatoms.

Unless otherwise stated, the term “heteroatom” as used herein representsat least one of N, O, S, P, and Si.

Unless otherwise stated, the term “aliphatic” as used herein means analiphatic hydrocarbon having 1 to 60 carbon atoms, and the term“aliphatic ring” as used herein means an aliphatic hydrocarbon ringhaving 3 to 60 carbon atoms.

Unless otherwise stated, the term “saturated or unsaturated ring” meansa saturated or unsaturated aliphatic ring, an aromatic ring having 6 to60 carbon atoms, or a hetero ring.

Hetero compounds or hetero radicals other than the above-mentionedhetero compounds each contain, but not limited to, one or moreheteroatoms.

Unless otherwise stated, the term “substituted or unsubstituted” as usedherein means that substitution is carried out by at least onesubstituent selected from the group consisting of, but not limited to,deuterium, halogen, an amino group, a nitrile group, a nitro group, aC₁˜C₂₀ alkyl group, a C₁˜C₂₀ alkoxy group, a C₁˜C₂₀ alkylamine group, aC₁˜C₂₀ alkylthio group, a C₆˜C₂₀ arylthio group, a C₂˜C₂₀ alkenyl group,a C₂˜C₂₀ alkynyl group, a C₃˜C₂₀ cycloalkyl group, a C₆˜C₆₀ aryl group,a C₆˜-C₂₀ aryl group substituted by deuterium, a C₈˜C₂₀ arylalkenylgroup, a silane group, a boron group, a germanium group, and a C₅˜C₂₀heterocyclic group.

The FIGURE illustrates an organic electronic element according to anembodiment of the present invention.

Referring to the FIGURE, an organic electronic element 100 according tothe present invention includes a first electrode 120 formed on asubstrate 110, a second electrode 180, and an organic material layerbetween the first electrode 120 and the second electrode 180, whichcontains the compound represented by Formula 1. Here, the firstelectrode 120 may be an anode (positive electrode), and the secondelectrode 180 may be a cathode (negative electrode). In the case of aninverted organic electronic element, the first electrode may be acathode, and the second electrode may be an anode.

The organic material layer includes a hole injection layer 130, a holetransport layer 140, a light emitting layer 150, an electron transportlayer 160, and an electron injection layer 170 formed in sequence on thefirst electrode 120. Here, the layers included in the organic materiallayer, except the light emitting layer 150, may not be formed. Theorganic material layer may further include a hole blocking layer, anelectron blocking layer, an emission-auxiliary layer 151, a buffer layer141, etc., and the electron transport layer 160 and the like may serveas the hole blocking layer.

Although not shown, the organic electronic element according to thepresent invention may further include protective layer formed one sideof one the first and second electrodes, which is opposite to the organicmaterial layer.

The inventive compound employed in the organic material layer may beused as a host material, a dopant material, or a capping layer materialin the hole injection layer 130, the hole transport layer 140, theelectron transport layer 160, the electron injection layer 170, or thelight emitting layer 150.

The organic electronic element according to an embodiment of the presentinvention may be manufactured using a PVD (physical vapor deposition)method. For example, the organic electronic element may be manufacturedby depositing a metal, a conductive metal oxide, or a mixture thereof onthe substrate 110 to form the anode 120, forming the organic materiallayer including the hole injection layer 130, the hole transport layer140, the light emitting layer 150, the electron transport layer 160, andthe electron injection layer 170 thereon, and then depositing amaterial, which can be used as the cathode 180, thereon.

Also, the organic material layer may be manufactured in such a mannerthat a smaller number of layers are formed using various polymermaterials by means of a soluble process or solvent process, for example,spin coating, dip coating, doctor blading, screen printing, inkjetprinting, or thermal transfer, instead of deposition. Since the organicmaterial layer according to the present invention may be formed invarious ways, the scope of protection of the present invention is notlimited by a method of forming the organic material layer.

According to used materials, the organic electronic element according tothe present invention may be of a top emission type, a bottom emissiontype, or a dual emission type.

Further, the organic electronic element according to the presentinvention may be any one of an organic light emitting diode (OLED), anorganic solar cell, an organic photo conductor (OPC), an organictransistor (organic TFT), and an element for monochromatic or whiteillumination.

Another embodiment of the present invention provides an electronicdevice including a display device, which includes the above describedorganic electronic element, and a control unit for controlling thedisplay device. Here, the electronic device may be a wired/wirelesscommunication terminal which is currently used or will be used in thefuture, and covers all kinds of electronic devices including a mobilecommunication terminal such as a cellular phone, a PDA, an electronicdictionary, a PMP, a remote controller, a navigation unit, a gameplayer, various kinds of TVs, and various kinds of computers.

Hereinafter, a compound according to an aspect of the present inventionwill be described.

The compound according to an aspect of the present invention isrepresented by Formula 1 below.

In Formula 1, Rings A and B are each independently a C₆˜C₁₀ aromaticgroup, and phenyl, naphthalene, or the like may belong thereto. Here,both of rings A and B may be naphthalene, or both of rings A and B maynot be naphthalene, that is, ring B may be naphthalene when ring A isphenyl, and ring A may be naphthalene when ring B is phenyl.

In addition, L may be selected from the group consisting of a singlebond; a C₆˜C₆₀ arylene group; a fluorenylene group; a C₂˜C₆₀heterocyclic group containing at least one heteroatom of O, N, S, Si,and P; and a divalent aliphatic hydrocarbon group, and for example,phenylene, naphthalene, or the like may belong thereto.

Here, the single bond means the absence of L, and it can be seen fromFormulas 1-1, 1-37, and 1-40 of the present invention that L is absent.

In addition, Ar₁ and Ar₂ are each independently selected from the groupconsisting of a fluorenyl group; a silane group; a C₆˜C₆₀ aryl group; aC₂˜C₂₀ alkenyl group; a C₂˜C₆₀ heterocyclic group containing at leastone heteroatom of O, N, S, Si, and P; a C₁˜C₅₀ alkyl group; and a fusedcyclic group of a C₆˜C₆₀ aromatic ring and a C₃˜C₆₀ aliphatic ring.

In addition, X₁ to X₄ are each independently CR′ or N; and R′ may beselected from the group consisting of hydrogen; a C₆˜C₆₀ aryl group; afluorenyl group; a C₂˜C₆₀ heterocyclic group containing at least oneheteroatom of O, N, S, Si, and P; a C₁˜-C₅₀ alkyl group; and a fusedcyclic group of a C₆˜C₆₀ aromatic ring and a C₃˜C₆₀ aliphatic ring; anda C₂˜C₂₀ alkenyl group.

Meanwhile, ring A, ring B, Ar₁, Ar₂, and R′ may be further substitutedwith other substituents.

That is, when the aryl group, fluorenyl group, heterocyclic group, fusedcyclic group, alkyl group, alkenyl group, aromatic group, aliphatichydrocarbon group, arylene group, and fluorenylene group are furthersubstituted with at least one substituent, each of the groups may befurther substituted with at least one substituent selected from thegroup consisting of: deuterium; halogen; a silane group; a siloxanegroup; a boron group; a germanium group; a cyano group; a nitro group;an amine group; a C₁˜-C₂₀ alkylthio group; a C₁˜-C₂₀ alkoxy group; aC₁˜C₂₀ alkyl group; a C₂˜C₂₀ alkenyl group; a C₂˜C₂₀ alkynyl group; aC₆˜C₂₀ aryl group; a C₆˜C₂₀ aryl group substituted with deuterium; afluorenyl group; a C₂˜C₂₀ heterocyclic group; a C₃˜C₂₀ cycloalkyl group;a C₇˜C₂₀ arylalkyl group, and a C₈˜C₂₀ arylalkenyl group.

Meanwhile, Formula 1 above may be represented by one of the compoundsbelow.

Here, in the Formulas 2 to 9 above, Ar₁, Ar₂, X₁ to X₄, and L aredefined as in Formula 1.

Meanwhile, Formulas 1 to 9 above may be represented by one of thecompounds below.

Hereinafter, synthesis examples of the compound represented by Formula 1and manufacturing examples of the organic electronic element accordingto the present invention will be described in detail by way of example.However, the following examples are only for illustrative purposes andare not intended to limit the scope of the invention.

SYNTHESIS EXAMPLES

By way of example, the inventive compound (final product) is prepared bya reaction of sub 1 and sub 2 as shown in Reaction Scheme 1 below.

1. Synthesis of Sub 1

Sub 1 may be synthesized by a reaction pathway of Reaction Scheme 2below.

Synthesis examples of specific compounds belonging to Sub 1 are asfollows.

(1) Synthesis example of Sub 1-1 (L=single bond)

Synthesis of Intermediate M 1-I-1

Astartingmaterial, phenylboronicacid (89.06 g, 730.4 mmol) was dissolvedin THF in a round bottom flask, and then 2-iodo-1-nitronaphthalene(262.13 g, 876.5 mmol), Pd(PPh₃)₄ (42.20 g, 36.5 mmol), K₂CO₃ (302.85 g,2191.3 mmol), and water were added, followed by stirring at 80□. Uponcompletion of the reaction, the reaction product was extracted withCH₂Cl₂ and water. The organic layer was dried over MgSO₄ andconcentrated, and then the thus generated compound was subjected to asilica gel column and recrystallization to give a product 158.4 g(yield: 87%).

Synthesis of Intermediate M 1-II-1

M 1-I-1 (158.4 g, 635.5 mmol) obtained in the above synthesis wasdissolved in o-dichlorobenzene in a round bottom flask, and thentriphenylphosphine (416.7 g, 1588.7 mmol) was added, followed bystirring at 200□. Upon completion of the reaction, o-dichlorobenzene wasremoved through distillation, followed by extraction with CH₂Cl₂ andwater. The organic layer was dried over MgSO₄ and concentrated, and thenthe thus generated compound was subjected to a silica gel column andrecrystallization to give a product 102.17 g (yield: 74%).

Synthesis of Intermediate Sub 1-I-1

After M 1-II-1 (102.17 g, 470.2 mmol) obtained in the above synthesiswas dissolved in chloroform in a round bottom flask, the temperature ofthe reaction material was lowered to 0□, and then N-bromosuccinimide(83.70 g, 470.2 mmol) was slowly added dropwise, followed by stirring atroom temperature. Upon completion of the reaction, the reaction productwas extracted with CH₂Cl₂ and water. The organic layer was dried overMgSO₄ and concentrated, and then the thus generated compound wassubjected to a silica gel column and recrystallization to give a product90.52 g (yield: 65%).

Synthesis of Intermediate Sub 1-II-1

Sub 1-I-1 (90.52 g, 305.6 mmol) obtained in the above synthesis wasdissolved in nitrobenzene in a round bottom flask, and then iodobenzene(93.53 g, 458.5 mmol), Na₂SO₄ (43.41 g, 305.6 mmol), K₂CO₃ (42.24 g,305.6 mmol), and Cu (5.83 g, 91.7 mmol) were added, followed by stirringat 200□. Upon completion of the reaction, nitrobenzene was removedthrough distillation, followed by extraction with CH₂Cl₂ and water. Theorganic layer was dried over MgSO₄ and concentrated, and then the thusgenerated compound was subjected to a silica gel column andrecrystallization to give a product 83.06 g (yield: 73%).

Synthesis of Intermediate Sub 1-III-1

Sub 1-II-1 (83.06 g, 223.1 mmol) obtained in the above synthesis wasdissolved in DMF in a round bottom flask, and thenBis(pinacolato)diboron (62.33 g, 245.4 mmol), Pd(dppf)Cl₂ (5.47 g, 6.7mmol), and KOAc (65.69 g, 669.4 mmol) were added, followed by stirringat 90□. Upon completion of the reaction, DMF was removed throughdistillation, followed by extraction with CH₂Cl₂ and water. The organiclayer was dried over MgSO₄ and concentrated, and then the thus generatedcompound was subjected to a silica gel column and recrystallization togive a product 79.53 g (yield: 85%).

Synthesis Example of Sub 1-1

Sub 1-III-1 (50.21 g, 119.7 mmol) obtained in the above synthesis wasdissolved in THF in a round bottom flask, and then 3-bromo-9H-carbazole(35.36 g, 143.7 mmol), Pd(PPh₃)₄ (6.92 g, 6 mmol), K₂CO₃ (49.65 g, 359.2mmol), and water were added, followed by stirring at 80□. Uponcompletion of the reaction, the reaction product was extracted withCH₂Cl₂ and water. The organic layer was dried over MgSO₄ andconcentrated, and then the thus generated compound was subjected to asilica gel column and recrystallization to give a product 40.63 g(yield: 74%).

(2) Synthesis example of Sub 1-18

Synthesis of Intermediate Sub 1-IV-18

Sub 1-III-1 (29.32 g, 69.9 mmol) obtained in the above synthesis wasdissolved in THF in a round bottom flask, and then 1-bromo-4-iodobenzene(29.67 g, 104.9 mmol), Pd(PPh₃)₄ (4.04 g, 3.5 mmol), K₂CO₃ (28.99 g,209.8 mmol), and water were added, followed by stirring at 80□. Uponcompletion of the reaction, the reaction product was extracted withCH₂Cl₂ and water. The organic layer was dried over MgSO₄ andconcentrated, and then the thus generated compound was subjected to asilica gel column and recrystallization to give a product 24.45 g(yield: 78%).

Synthesis of Intermediate Sub 1-V-18

Sub 1-IV-18 (24.45 g, 54.5 mmol) obtained in the above synthesis wasdissolved in DMF in a round bottom flask, and thenBis(pinacolato)diboron (15.23 g, 60 mmol), Pd(dppf)Cl₂ (1.34 g, 1.6mmol), and KOAc (16.06 g, 163.6 mmol) were added, followed by stirringat 90□. Upon completion of the reaction, DMF was removed throughdistillation, followed by extraction with CH₂Cl₂ and water. The organiclayer was dried over MgSO₄ and concentrated, and then the thus generatedcompound was subjected to a silica gel column and recrystallization togive a product 23.23 g (yield: 86%).

Synthesis Example of Sub 1-18

Sub 1-V-18 (23.23 g, 46.9 mmol) obtained in the above synthesis wasdissolved in THF in a round bottom flask, and then 2-bromo-9H-carbazole(13.85 g, 56.3 mmol), Pd(PPh₃)₄ (2.71 g, 2.3 mmol) K₂CO₃ (19.44 g, 140.7mmol), and water were added, followed by stirring at 80□. Uponcompletion of the reaction, the reaction product was extracted withCH₂Cl₂ and water. The organic layer was dried over MgSO₄ andconcentrated, and then the thus generated compound was subjected to asilica gel column and recrystallization to give a product 20.06 g(yield: 80%).

(3) Synthesis example of Sub 1-22 (L-single bond)

Synthesis of Intermediate Sub 1-I-22

In addition to 9H-carbazole (108.76 g, 650.4 mmol) as a startingmaterial, N-bromosuccinimide (115.77 g, 650.4 mmol) and chloroform wereused according to the synthesis method of Sub 1-I-1 of Example 1 above,to give a product 112.05 g (yield: 70%).

Synthesis of Intermediate Sub 1-II-22

In addition to Sub 1-I-22 (112.05 g, 455.3 mmol) obtained in the abovesynthesis, iodobenzene (139.33 g, 683 mmol), Na₂SO₄ (64.67 g, 455.3mmol), K₂CO₃ (62.93 g, 455.3 mmol), Cu (8.68 g, 136.6 mmol), andnitrobenzene were used according to the synthesis method of Sub 1-II-1of Example 1 above, to give a product 110.02 g (yield: 75%).

Synthesis of Intermediate Sub 1-III-22

In addition to Sub 1-II-22 (110.02 g, 341.5 mmol) obtained in the abovesynthesis, Bis(pinacolato)diboron (95.38 g, 375.6 mmol), Pd(dppf)Cl₂(8.37 g, 10.2 mmol), KOAc (100.53 g, 1024.4 mmol), and DMF were usedaccording to the synthesis method of Sub 1-III-1 of Example 1 above, togive a product 105.92 g (yield: 84%).

Synthesis Example of Sub 1-22

In addition to Sub 1-III-22 (55.3 g, 149.8 mmol) obtained in the abovesynthesis, 5-bromo-11H-benzo[a] carbazole (53.22 g, 179.7 mmol),Pd(PPh₃)₄ (8.65 g, 7.5 mmol), K₂CO₃ (62.09 g, 449.3 mmol), THF, andwater were used according to the synthesis method of Sub 1-1 of Example1 above, to give a product 48.76 g (yield: 71%).

(4) Synthesis Example of Sub 1-32 (L=single bond)

Synthesis of Intermediate M 2-I-32

A starting material, phenylboronic acid (89.13 g, 731 mmol) wasdissolved in THF in a round bottom flask, and then4-dibromo-2-nitrobenzene (308 g, 1096.5 mmol), Pd(PPh₃)₄ (42.24 g, 36.5mmol), K₂CO₃ (303.09 g, 2193 mmol), and water were added, followed bystirring at 80□. Upon completion of the reaction, the reaction productwas extracted with CH₂Cl₂ and water. The organic layer was dried overMgSO₄ and concentrated, and then the thus generated compound wassubjected to a silica gel column and recrystallization to give a product128.07 g (yield: 63%).

Synthesis of Intermediate Sub 1-I-32

M 2-I-32 (128.07 g, 460.5 mmol) obtained in the above synthesis wasdissolved in o-dichlorobenzene in a round bottom flask, and thentriphenylphosphine (301.97 g, 1151.3 mmol) was added, followed bystirring at 200□. Upon completion of the reaction, o-dichlorobenzene wasremoved through distillation, followed by extraction with CH₂Cl₂ andwater. The organic layer was dried over MgSO₄ and concentrated, and thenthe thus generated compound was subjected to a silica gel column andrecrystallization to give a product 80.47 g (yield: 71%).

Synthesis of Intermediate Sub 1-II-32

In addition to Sub 1-I-32 (80.47 g, 327 mmol) obtained in the abovesynthesis, iodobenzene (100.06 g, 490.5 mmol), Na₂SO₄ (46.44 g, 327mol), K₂CO₃ (45.19 g, 327 mmol), Cu (6.23 g, 98.1 mmol), andnitrobenzene were used according to the synthesis method of Sub 1-II-1of Example 1 above, to give a product 76.91 g (yield: 73%).

Synthesis of Intermediate Sub 1-III-32

In addition to Sub 1-II-32 (76.91 g, 238.7 mmol) obtained in the abovesynthesis, Bis(pinacolato)diboron (66.68 g, 262.6 mmol), Pd (dppf) Cl₂(5.85 g, 7.2 mmol), KOAc (70.28 g, 716.1 mmol), and DMF were usedaccording to the synthesis method of Sub 1-III-1 of Example 1 above, togive a product 69.63 g (yield: 79%).

Synthesis Example of Sub 1-32

In addition to Sub 1-III-32 (69.63 g, 188.6 mmol) obtained in the abovesynthesis, 5-bromo-11H-benzo[a] carbazole (67.01 g, 226.3 mmol),Pd(PPh₃)₄ (10.89 g, 9.4 mmol), K₂CO₃ (78.19 g, 565.7 mmol), THF, andwater were used according to the synthesis method of Sub 1-1 of Example1 above, to give a product 61.39 g (yield: 71%).

(5) Synthesis Example of Sub 1-46 (L=single bond)

Synthesis of Intermediate M 2-I-47

In addition to phenylboronic acid (90.24 g, 740.1 mmol) as a startingmaterial, 1,4-dibromo-2-nitronaphthalene (367.41 g, 1110.1 mmol),Pd(PPh₃)₄ (42.76 g, 37 mmol), K₂CO₃ (306.87 g, 2220.3 mmol), THF, andwater were used according to the synthesis method of M 2-I-32 of Example1, to give a product 148.15 g (yield: 61%).

Synthesis of Intermediate Sub 1-I-47

In addition to M 2-I-47 (148.15 g, 451.5 mmol) obtained in the abovesynthesis, triphenylphosphine (296.03 g, 1128.6 mmol) ando-dichlorobenzene were used according to the synthesis method of Sub1-I-32 of Example 1, to give a product 92.26 g (yield: 69%).

Synthesis of Intermediate Sub 1-II-47

In addition to Sub 1-I-47 (92.26 g, 311.5 mmol) obtained in the abovesynthesis, 4-iodo-1,1′-biphenyl (130.89 g, 467.3 mmol), Na₂SO₄ (44.25 g,311.5 mmol), K₂CO₃ (43.06 g, 311.5 mmol), Cu (5.94 g, 93.5 mmol), andnitrobenzene were used according to the synthesis method of Sub 1-II-1of Example 1 above, to give a product 100.56 g (yield: 72%).

Synthesis of Intermediate Sub 1-III-47

In addition to Sub 1-II-47 (100.56 g, 224.3 mmol) obtained in the abovesynthesis, Bis(pinacolato)diboron (62.65 g, 246.7 mmol), Pd(dppf)Cl₂(5.49 g, 6.7 mmol), KOAc (66.04 g, 672.9 mmol), and DMF were usedaccording to the synthesis method of Sub 1-III-1 of Example 1 above, togive a product 85.56 g (yield: 77%).

Synthesis Example of Sub 1-47

In addition to Sub 1-III-47 (46.97 g, 94.8 mmol) obtained in the abovesynthesis, 5-bromo-11H-benzo[a]carbazole (33.69 g, 113.8 mmol),Pd(PPh₃)₄ (5.48 g, 4.7 mmol), K₂CO₃ (39.31 g, 284.4 mmol), THF, andwater were used according to the synthesis method of Sub 1-1 of Example1 above, to give a product 34.37 g (yield: 62%).

(6) Synthesis Example of Sub 1-52 (L-single bond)

In addition to Sub 1-III-47 (38.59 g, 77.9 mmol) obtained in the abovesynthesis, 3-bromo-9H-carbazole (23 g, 93.5 mmol), Pd(PPh₃)₄ (4.5 g, 3.9mmol), K₂CO₃ (32.3 g, 233.7 mmol), THF, and water were used according tothe synthesis method of Sub 1-1 of Example 1 above, to give a product30.4 g (yield: 73%).

(7) Synthesis example of Sub 1-76

Synthesis of Intermediate Sub 1-IV-76

In addition to Sub 1-III-22 (50.62 g, 137.1 mmol) obtained in the abovesynthesis, 2-bromo-6-iodonaphthalene (68.47 g, 205.6 mmol), Pd(PPh₃)₄(7.92 g, 6.9 mmol), K₂CO₃ (56.84 g, 411.3 mmol), THF, and water wereused according to the synthesis method of Sub 1-IV-18 of Example 1above, to give a product 44.87 g (yield: 73%).

Synthesis of Intermediate Sub 1-V-76

In addition to Sub 1-IV-76 (44.87 g, 100.1 mmol) obtained in the abovesynthesis, Bis(pinacolato)diboron (27.96 g, 110.1 mmol), Pd(dppf)Cl₂(2.45 g, 3 mmol), KOAc (29.46 g, 300.2 mmol), and DMF were usedaccording to the synthesis method of Sub 1-V-18 of Example 1 above, togive a product 40.16 g (yield: 81%).

Synthesis Example of Sub 1-76

In addition to Sub 1-V-76 (40.16 g, 81.1 mmol) obtained in the abovesynthesis, 5-bromo-7H-benzo[c]carbazole (28.81 g, 97.3 mmol), Pd(PPh₃)₄(4.68 g, 4.1 mmol), K₂CO₃ (33.61 g, 243.2 mmol), THF, and water wereused according to the synthesis method of Sub 1-18 of Example 1 above,to give a product 35.07 g (yield: 74%).

Meanwhile, examples of Sub 1 are as follows, but are limited thereto,and FD-MS values thereof are shown in Table 1 below.

TABLE 1 Compound FD-MS Compound FD-MS Sub 1-1 m/z = 458.18 (C₃₄H₂₂N₂ =458.55) Sub 1-2 m/z = 508.19 (C₃₈H₂₄N₂ = 508.61) Sub 1-3 m/z = 534.21(C₄₀H₂₆N₂ = 534.65) Sub 1-4 m/z = 574.24 (C₄₃H₃₀N₂ = 574.71) Sub 1-5 m/z= 459.17 (C₃₃H₂₁N₃ = 459.54) Sub 1-6 m/z = 410.18 (C₃₀H₂₂N₂ = 410.51)Sub 1-7 m/z = 534.21 (C₄₀H₂₆N₂ = 534.65) Sub 1-8 m/z = 534.21 (C₄₀H₂₆N₂= 534.65) Sub 1-9 m/z = 584.23 (C₄₄H₂₈N₂ = 584.71) Sub 1-10 m/z = 584.23(C₄₄H₂₈N₂ = 584.71) Sub 1-11 m/z = 458.18 (C₃₄H₂₂N₂ = 458.55) Sub 1-12m/z = 508.19 (C₃₈H₂₄N₂ = 508.61) Sub 1-13 m/z = 534.21 (C₄₀H₂₆N₂ =534.65) Sub 1-14 m/z = 574.24 (C₄₃H₃₀N₂ = 574.71) Sub 1-15 m/z = 459.17(C₃₃H₂₁N₃ = 459.54) Sub 1-16 m/z = 410.18 (C₃₀H₂₂N₂ = 410.51) Sub 1-17m/z = 472.19 (C₃₅H₂₄N₂ = 472.58) Sub 1-18 m/z = 534.21 (C₄₀H₂₆N₂ =534.65) Sub 1-19 m/z = 610.24 (C₄₆H₃₀N₂ = 610.74) Sub 1-20 m/z = 584.23(C₄₄H₂₈N₂ = 584.71) Sub 1-21 m/z = 584.23 (C₄₄H₂₈N₂ = 584.71) Sub 1-22m/z = 458.18 (C₃₄H₂₂N₂ = 458.55) Sub 1-23 m/z = 508.19 (C₃₈H₂₄N₂ =508.61) Sub 1-24 m/z = 534.21 (C₄₀H₂₆N₂ = 534.65) Sub 1-25 m/z = 574.24(C₄₃H₃₀N₂ = 574.71) Sub 1-26 m/z = 459.17 (C₃₃H₂₁N₃ = 459.54) Sub 1-27m/z = 410.18 (C₃₀H₂₂N₂ = 410.51) Sub 1-28 m/z = 534.21 (C₄₀H₂₆N₂ =534.65) Sub 1-29 m/z = 534.21 (C₄₀H₂₆N₂ = 534.65) Sub 1-30 m/z = 584.23(C₄₄H₂₈N₂ = 584.71) Sub 1-31 m/z = 584.23 (C₄₄H₂₈N₂ = 584.71) Sub 1-32m/z = 458.18 (C₃₄H₂₂N₂ = 458.55) Sub 1-33 m/z = 508.19 (C₃₈H₂₄N₂ =508.61) Sub 1-34 m/z = 534.21 (C₄₀H₂₆N₂ = 534.65) Sub 1-35 m/z = 574.24(C₄₃H₃₀N₂ = 574.71) Sub 1-36 m/z = 459.17 (C₃₃H₂₁N₃ = 459.54) Sub 1-37m/z = 410.18 (C₃₀H₂₂N₂ = 410.51) Sub 1-38 m/z = 534.21 (C₄₀H₂₆N₂ =534.65) Sub 1-39 m/z = 610.24 (C₄₆H₃₀N₂ = 610.74) Sub 1-40 m/z = 508.19(C₃₈H₂₄N₂ = 508.61) Sub 1-41 m/z = 558.21 (C₄₂H₂₆N₂ = 558.67) Sub 1-42m/z = 584.23 (C₄₄H₂₈N₂ = 584.71) Sub 1-43 m/z = 585.22 (C₄₃H₂₇N₃ =585.69) Sub 1-44 m/z = 634.24 (C₄₈H₃₀N₂ = 634.77) Sub 1-45 m/z = 508.19(C₃₈H₂₄N₂ = 508.61) Sub 1-46 m/z = 558.21 (C₄₂H₂₆N₂ = 558.67) Sub 1-47m/z = 584.23 (C₄₄H₂₈N₂ = 584.71) Sub 1-48 m/z = 584.23 (C₄₄H₂₈N₂ =584.71) Sub 1-49 m/z = 634.24 (C₄₈H₃₀N₂ = 634.77) Sub 1-50 m/z = 458.18(C₃₄H₂₂N₂ = 458.55) Sub 1-51 m/z = 508.19 (C₃₈H₂₄N₂ = 508.61) Sub 1-52m/z = 534.21 (C₄₀H₂₆N₂ = 534.65) Sub 1-53 m/z = 574.24 (C₄₃H₃₀N₂ =574.71) Sub 1-54 m/z = 459.17 (C₃₃H₂₁N₃ = 459.54) Sub 1-55 m/z = 534.21(C₄₀H₂₆N₂ = 534.65) Sub 1-56 m/z = 534.21 (C₄₀H₂₆N₂ = 534.65) Sub 1-57m/z = 584.23 (C₄₄H₂₈N₂ = 584.71) Sub 1-58 m/z = 584.23 (C₄₄H₂₈N₂ =584.71) Sub 1-59 m/z = 458.18 (C₃₄H₂₂N₂ = 458.55) Sub 1-60 m/z = 508.19(C₃₈H₂₄N₂ = 508.61) Sub 1-61 m/z = 534.21 (C₄₀H₂₆N₂ = 534.65) Sub 1-62m/z = 574.24 (C₄₃H₃₀N₂ = 574.71) Sub 1-63 m/z = 459.17 (C₃₃H₂₁N₃ =459.54) Sub 1-64 m/z = 534.21 (C₄₀H₂₆N₂ = 534.65) Sub 1-65 m/z = 534.21(C₄₀H₂₆N₂ = 534.65) Sub 1-66 m/z = 584.23 (C₄₄H₂₈N₂ = 584.71) Sub 1-67m/z = 584.23 (C₄₄H₂₈N₂ = 584.71) Sub 1-68 m/z = 458.18 (C₃₄H₂₂N₂ =458.55) Sub 1-69 m/z = 508.19 (C₃₈H₂₄N₂ = 508.61) Sub 1-70 m/z = 534.21(C₄₀H₂₆N₂ = 534.65) Sub 1-71 m/z = 574.24 (C₄₃H₃₀N₂ = 574.71) Sub 1-72m/z = 459.17 (C₃₃H₂₁N₃ = 459.54) Sub 1-73 m/z = 534.21 (C₄₀H₂₆N₂ =534.65) Sub 1-74 m/z = 534.21 (C₄₀H₂₆N₂ = 534.65) Sub 1-75 m/z = 584.23(C₄₄H₂₈N₂ = 584.71) Sub 1-76 m/z = 584.23 (C₄₄H₂₈N₂ = 584.71) Sub 1-77m/z = 458.18 (C₃₄H₂₂N₂ = 458.55) Sub 1-78 m/z = 508.19 (C₃₈H₂₄N₂ =508.61) Sub 1-79 m/z = 534.21 (C₄₀H₂₆N₂ = 534.65) Sub 1-80 m/z = 574.24(C₄₃H₃₀N₂ = 574.71) Sub 1-81 m/z = 459.17 (C₃₃H₂₁N₃ = 459.54) Sub 1-82m/z = 534.21 (C₄₀H₂₆N₂ = 534.65) Sub 1-83 m/z = 534.21 (C₄₀H₂₆N₂ =534.65) Sub 1-84 m/z = 584.23 (C₄₄H₂₈N₂ = 584.71) Sub 1-85 m/z = 584.23(C₄₄H₂₈N₂ = 584.71) Sub 1-86 m/z = 508.19 (C₃₈H₂₄N₂ = 508.61) Sub 1-87m/z = 558.21 (C₄₂H₂₆N₂ = 558.67) Sub 1-88 m/z = 584.23 (C₄₄H₂₈N₂ =584.71) Sub 1-89 m/z = 585.22 (C₄₃H₂₇N₃ = 585.69) Sub 1-90 m/z = 634.24(C₄₈H₃₀N₂ = 634.77) Sub 1-91 m/z = 508.19 (C₃₈H₂₄N₂ = 508.61) Sub 1-92m/z = 558.21 (C₄₂H₂₆N₂ = 558.67) Sub 1-93 m/z = 584.23 (C₄₄H₂₈N₂ =584.71) Sub 1-94 m/z = 584.23 (C₄₄H₂₈N₂ = 584.71) Sub 1-95 m/z = 634.24(C₄₈H₃₀N₂ = 634.77)2. Synthesis of Sub 2

Sub 2 of Reaction Scheme 1 may be synthesized by a reaction pathway ofReaction Scheme 10 below.

Synthesis examples of specific compounds belonging to Sub 2 are asfollows.

(1) Synthesis example of Sub 2-2

A starting material, 2,4-dichloroquinazoline (89.57 g, 450 mmol) wasdissolved in THF in a round bottom flask, and then phenylboronic acid(65.84 g, 540 mmol), Pd(PPh₃)₄ (26 g, 22.5 mmol), K₂CO₃ (186.59 g, 1350mmol), and water were added, followed by stirring at 70□. Uponcompletion of the reaction, the reaction product was extracted withCH₂Cl₂ and water. The organic layer was dried over MgSO₄ andconcentrated, and then the thus generated compound was subjected to asilica gel column and recrystallization to give a product 71.49 g(yield: 66%).

(2) Synthesis example of Sub 2-8

In addition to 2,4-dichloroquinazoline (76.59 g, 384.8 mmol) as astarting material, [1,1′-biphenyl]-4-ylboronic acid (91.44 g, 461.8mmol), Pd(PPh₃)₄ (22.23 g, 19.2 mmol), K₂CO₃ (159.55 g, 1154.4 mmol),THF, and water were used according to the synthesis method of Sub 2-2 ofExample 1, to give a product 74.36 g (yield: 61%).

(3) Synthesis example of Sub 2-14

In addition to 2,4-dichloroquinazoline (78.48 g, 394.3 mmol) as astarting material, naphthalen-2-ylboronic acid (81.38 g, 473.2 mmol),Pd(PPh₃)₄ (22.78 g, 19.7 mmol), K₂CO₃ (163.49 g, 1182.9 mmol), THF, andwater were used according to the synthesis method of Sub 2-2 of Example1, to give a product 73.37 g (yield: 64%).

(4) Synthesis Example of Sub 2-27

In addition to 2,4-dichloroquinazoline (70.43 g, 353.8 mmol) as astarting material, dibenzo[b,d]thiophen-2-ylboronic acid (96.84 g, 424.6mmol), Pd(PPh₃)₄ (20.44 g, 17.7 mmol), K₂CO₃ (146.72 g, 1061.5 mmol),THF, and water were used according to the synthesis method of Sub 2-2 ofExample 1, to give a product 77.32 g (yield: 63%).

(5) Synthesis Example of Sub 2-29

In addition to 2,4-dichloropyrido[3,2-d]pyrimidine (85.21 g, 426 mmol)as a starting material, phenylboronic acid (62.33 g, 511.2 mmol),Pd(PPh₃)₄ (24.61 g, 21.3 mmol), K₂CO₃ (176.64 g, 1278 mmol), THF, andwater were used according to the synthesis method of Sub 2-2 of Example1, to give a product 55.6 g (yield: 54%).

(6) Synthesis example of Sub 2-34

In addition to 2,4-dichloropyrido[2,3-d]pyrimidine (71.05 g, 355.2 mmol)as a starting material, [1,1′-biphenyl]-4-ylboronic acid (84.41 g, 426.3mmol), Pd(PPh₃)₄ (20.52 g, 17.8 mmol), K₂CO₃ (147.28 g, 1065.6 mmol),THF, and water were used according to the synthesis method of Sub 2-2 ofExample 1, to give a product 58.7 g (yield: 52%).

Meanwhile, examples of Sub 2 are as follows, but are not limitedthereto, and FD-MS values thereof are shown in Table 2 below.

TABLE 2 Compound FD-MS Compound FD-MS Sub 2-1 m/z = 178.03 (C₉H₇ClN₂ =178.62) Sub 2-2 m/z = 240.05 (C₁₄H₉ClN₂ = 240.69) Sub 2-3 m/z = 254.06(C₁₅H₁₁ClN₂ = 254.71) Sub 2-4 m/z = 254.06 (C₁₅H₁₁ClN₂ = 254.71) Sub 2-5m/z = 268.08 (C₁₆H₁₃ClN₂ = 268.74) Sub 2-6 m/z = 245.08 (C₁₄H₄D₅ClN₂ =245.72) Sub 2-7 m/z = 241.04 (C₁₃H₈ClN₃ = 241.68) Sub 2-8 m/z = 316.08(C₂₀H₁₃ClN₂ = 316.78) Sub 2-9 m/z = 316.08 (C₂₀H₁₃ClN₂ = 316.78) Sub2-10 m/z = 366.09 (C₂₄H₁₅ClN₂ = 366.84) Sub 2-11 m/z = 366.09(C₂₄H₁₅ClN₂ = 366.84) Sub 2-12 m/z = 366.09 (C₂₄H₁₅ClN₂ = 366.84) Sub2-13 m/z = 290.06 (C₁₈H₁₁ClN₂ = 290.75) Sub 2-14 m/z = 290.06(C₁₉H₁₁ClN₂ = 290.75) Sub 2-15 m/z = 304.08 (C₁₉H₁₃ClN₂ = 304.77) Sub2-16 m/z = 366.09 (C₂₄H₁₅ClN₂ = 366.84) Sub 2-17 m/z = 366.09(C₂₄H₁₅ClN₂ = 366.84) Sub 2-18 m/z = 366.09 (C₂₄H₁₅ClN₂ = 366.84) Sub2-19 m/z = 366.09 (C₂₄H₁₅ClN₂ = 366.84) Sub 2-20 m/z = 340.08(C₂₂H₁₃ClN₂ = 340.81) Sub 2-21 m/z = 340.08 (C₂₂H₁₃ClN₂ = 340.81) Sub2-22 m/z = 356.11 (C₂₃H₁₇ClN₂ = 356.85) Sub 2-23 m/z = 405.1 (C₂₆H₁₆ClN₃= 405.88) Sub 2-24 m/z = 405.1 (C₂₆H₁₆ClN₃ = 405.88) Sub 2-25 m/z =330.06 (C₂₀H₁₁ClN₂O = 330.77) Sub 2-26 m/z = 330.06 (C₂₀H₁₁ClN₂O =330.77) Sub 2-27 m/z = 346.03 (C₂₀H₁₁ClN₂S = 346.83) Sub 2-28 m/z =346.03 (C₂₀H₁₁ClN₂S = 346.83) Sub 2-29 m/z = 241.04 (C₁₃H₈ClN₃ = 241.68)Sub 2-30 m/z = 317.07 (C₁₉H₁₂ClN₃ = 317.77) Sub 2-31 m/z = 291.06(C₁₇H₁₀ClN₃ = 291.73) Sub 2-32 m/z = 291.06 (C₁₇H₁₀ClN₃ = 291.73) Sub2-33 m/z = 241.04 (C₁₃H₈ClN₃ = 241.68) Sub 2-34 m/z = 317.07 (C₁₉H₁₂ClN₃= 317.77) Sub 2-35 m/z = 291.06 (C₁₇H₁₀ClN₃ = 291.73) Sub 2-36 m/z =291.06 (C₁₇H₁₀ClN₃ = 291.73)3. Final Product Synthesis

Sub 1 (1 eq.) was dissolved in toluene in a round bottom flask, and thenSub 2 (1.2 eq.), Pd₂(dba)₃ (0.03 eq.), P(t-Bu)₃ (0.08 eq.), and NaOt-Bu(3 eq.) were added, followed by stirring at 100□. Upon completion of thereaction, the reaction product was extracted with CH₂Cl₂ and water. Theorganic layer was dried over MgSO₄ and concentrated, and then the thusgenerated compound was subjected to a silica gel column andrecrystallization, to give a final product.

(1) Synthesis example of Product 1-1

Sub 1-1 (7.65 g, 16.7 mmol) obtained in the above synthesis wasdissolved in toluene in a round bottom flask, and then Sub 2-2 (4.82 g,20 mmol), Pd₂(dba)₃ (0.46 g, 0.5 mmol), 50% P(t-Bu)₃ (0.7 ml, 1.3 mmol),and NaOt-Bu (4.81 g, 50 mmol) were added, followed by stirring at 100□.Upon completion of the reaction, the reaction product was extracted withCH₂Cl₂ and water. The organic layer was dried over MgSO₄ andconcentrated, and then the thus generated compound was subjected to asilica gel column and recrystallization to give a product 7.96 g (yield:72%).

(2) Synthesis Example of Product 1-10

In addition to Sub 1-1 (6.94 g, 15.1 mmol) obtained in the abovesynthesis, Sub 2-27 (6.3 g, 18.2 mmol), Pd₂(dba)₃ (0.42 g, 0.5 mmol),50% P(t-Bu)₃ (0.6 ml, 1.2 mmol), NaOt-Bu (4.36 g, 45.4 mmol), andtoluene were used according to the synthesis method of Product 1-1 ofexample 3, to give a product 8.15 g (yield: 70%).

(3) Synthesis Example of Product 1-53

In addition to Sub 1-18 (7.74 g, 14.5 mmol) obtained in the abovesynthesis, Sub 2-2 (4.18 g, 17.4 mmol), Pd₂(dba)₃ (0.4 g, 0.4 mmol), 50%P(t-Bu)₃ (0.6 ml, 1.2 mmol), NaOt-Bu (4.17 g, 43.4 mmol), and toluenewere used according to the synthesis method of Product 1-1 of example 3,to give a product 7.81 g (yield: 73%).

(4) Synthesis example of Product 1-58

In addition to Sub 1-22 (7.06 g, 15.4 mmol) obtained in the abovesynthesis, Sub 2-8 (5.85 g, 18.5 mmol), Pd₂(dba)₃ (0.42 g, 0.5 mmol),50% P(t-Bu)₃ (0.6 ml, 1.2 mmol), NaOt-Bu (4.44 g, 46.2 mmol), andtoluene were used according to the synthesis method of Product 1-1 ofexample 3, to give a product 7.85 g (yield: 69%).

(5) Synthesis Example of Product 1-89

In addition to Sub 1-32 (7.54 g, 16.4 mmol) obtained in the abovesynthesis, Sub 2-14 (5.74 g, 19.7 mmol), Pd₂(dba)₃ (0.45 g, 0.5 mmol),50% P(t-Bu)₃ (0.6 ml, 1.3 mmol), NaOt-Bu (4.74 g, 49.3 mmol), andtoluene were used according to the synthesis method of Product 1-1 ofexample 3, to give a product 8.32 g (yield: 71%).

(6) Synthesis Example of Product 1-130

In addition to Sub 1-47 (8.29 g, 14.2 mmol) obtained in the abovesynthesis, Sub 2-2 (4.09 g, 17 mmol), Pd₂(dba)₃ (0.39 g, 0.4 mmol), 50%P(t-Bu)₃ (0.6 ml, 1.1 mmol), NaOt-Bu (4.09 g, 42.5 mmol), and toluenewere used according to the synthesis method of Product 1-1 of example 3,to give a product 7.61 g (yield: 68%).

(7) Synthesis Example of Product 1-133

In addition to Sub 1-1 (8.11 g, 17.7 mmol) obtained in the abovesynthesis, Sub 2-29 (5.13 g, 21.2 mmol), Pd₂(dba)₃ (0.49 g, 0.5 mmol),50% P(t-Bu)₃ (0.7 ml, 1.4 mmol), NaOt-Bu (5.1 g, 53.1 mmol), and toluenewere used according to the synthesis method of Product 1-1 of example 3,to give a product 7.28 g (yield: 62%).

(8) Synthesis Example of Product 1-136

In addition to Sub 1-1 (8.32 g, 18.1 mmol) obtained in the abovesynthesis, Sub 2-34 (6.92 g, 21.8 mmol), Pd₂(dba)₃ (0.5 g, 0.5 mmol),50% P(t-Bu)₃ (0.7 ml, 1.5 mmol), NaOt-Bu (5.23 g, 54.4 mmol), andtoluene were used according to the synthesis method of Product 1-1 ofexample 3, to give a product 7.92 g (yield: 59%).

(9) Synthesis Example of Product 2-14

In addition to Sub 1-52 (7.92 g, 14.8 mmol) obtained in the abovesynthesis, Sub 2-2 (4.28 g, 17.8 mmol), Pd₂(dba)₃ (0.41 g, 0.4 mmol),50% P(t-Bu)₃ (0.6 ml, 1.2 mmol), NaOt-Bu (4.27 g, 44.4 mmol), andtoluene were used according to the synthesis method of Product 1-1 ofexample 3, to give a product 7.22 g (yield: 66%).

(10) Synthesis Example of Product 2-60

In addition to Sub 1-76 (8.01 g, 13.7 mmol) obtained in the abovesynthesis, Sub 2-2 (3.96 g, 16.4 mmol), Pd₂(dba)₃ (0.38 g, 0.4 mmol),50% P(t-Bu)₃ (0.5 ml, 1.1 mmol), NaOt-Bu (3.95 g, 41.1 mmol), andtoluene were used according to the synthesis method of Product 1-1 ofexample 3, to give a product 7.46 g (yield: 69%).

Meanwhile, FD-MS values of inventive compounds 1-1 to 1-148 and 2-1 to2-120, which were prepared according to the synthesis examples above,are shown in Table 3 below.

TABLE 3 Compound FD-MS Compound FD-MS 1-1 m/z = 662.25 (C₄₈H₃₀N₄ =662.78) 1-2 m/z = 738.28 (C₅₄H₃₄N₄ = 738.87) 1-3 m/z = 762.28 (C₅₆H₃₄N₄= 762.90) 1-4 m/z = 712.26 (C₅₂H₃₂N₄ = 712.84) 1-5 m/z = 712.26(C₅₂H₃₂N₄ = 712.84) 1-6 m/z = 738.28 (C₅₄H₃₄N₄ = 738.87) 1-7 m/z =778.31 (C₅₇H₃₈N₄ = 778.94) 1-8 m/z = 768.23 (C₅₄H₃₂N₄S = 768.92) 1-9 m/z= 752.26 (C₅₄H₃₂N₄O = 752.86) 1-10 m/z = 768.23 (C₅₄H₃₂N₄S = 768.92)1-11 m/z = 752.26 (C₅₄H₃₂N₄O = 752.86) 1-12 m/z = 827.30 (C₆₀H₃₇N₅ =827.97) 1-13 m/z = 667.28 (C₄₈H₂₅D₅N₄ = 667.81) 1-14 m/z = 788.29(C₅₈H₃₆N₄ = 788.93) 1-15 m/z = 788.29 (C₅₈H₃₆N₄ = 788.93) 1-16 m/z =788.29 (C₅₈H₃₆N₄ = 788.93) 1-17 m/z = 788.29 (C₅₈H₃₆N₄ = 788.93) 1-18m/z = 712.26 (C₅₂H₃₂N₄ = 712.84) 1-19 m/z = 738.28 (C₅₄H₃₄N₄ = 738.87)1-20 m/z = 778.31 (C₅₇H₃₈N₄ = 778.94) 1-21 m/z = 739.27 (C₅₃H₃₃N₅ =739.86) 1-22 m/z = 664.26 (C₄₈H₃₂N₄ = 664.79) 1-23 m/z = 676.26(C₄₉H₃₂N₄ = 676.81) 1-24 m/z = 600.23 (C₄₃H₂₈N₄ = 600.71) 1-25 m/z =738.28 (C₅₄H₃₄N₄ = 738.87) 1-26 m/z = 738.28 (C₅₄H₃₄N₄ = 738.87) 1-27m/z = 788.29 (C₅₈H₃₆N₄ = 788.93) 1-28 m/z = 788.29 (C₅₈H₃₆N₄ = 788.93)1-29 m/z = 662.25 (C₄₈H₃₀N₄ = 662.78) 1-30 m/z = 738.28 (C₅₄H₃₄N₄ =738.87) 1-31 m/z = 762.28 (C₅₆H₃₄N₄ = 762.90) 1-32 m/z = 712.26(C₅₂H₃₂N₄ = 712.84) 1-33 m/z = 712.26 (C₅₂H₃₂N₄ = 712.84) 1-34 m/z =788.29 (C₅₈H₃₆N₄ = 788.93) 1-35 m/z = 778.31 (C₅₇H₃₈N₄ = 778.94) 1-36m/z = 768.23 (C₅₄H₃₂N₄S = 768.92) 1-37 m/z = 752.26 (C₅₄H₃₂N₄O = 752.86)1-38 m/z = 768.23 (C₅₄H₃₂N₄S = 768.92) 1-39 m/z = 752.26 (C₅₄H₃₂N₄O =752.86) 1-40 m/z = 827.30 (C₆₀H₃₇N₅ = 827.97) 1-41 m/z = 667.28(C₄₈H₂₅D₅N₄ = 667.81) 1-42 m/z = 788.29 (C₅₈H₃₆N₄ = 788.93) 1-43 m/z =788.29 (C₅₈H₃₆N₄ = 788.93) 1-44 m/z = 788.29 (C₅₈H₃₆N₄ = 788.93) 1-45m/z = 788.29 (C₅₈H₃₆N₄ = 788.93) 1-46 m/z = 712.26 (C₅₂H₃₂N₄ = 712.84)1-47 m/z = 738.28 (C₅₄H₃₄N₄ = 738.87) 1-48 m/z = 778.31 (C₅₇H₃₈N₄ =778.94) 1-49 m/z = 739.27 (C₅₃H₃₃N₅ = 739.86) 1-50 m/z = 664.26(C₄₈H₃₂N₄ = 664.79) 1-51 m/z = 690.28 (C₅₀H₃₄N₄ = 690.83) 1-52 m/z =690.28 (C₅₀H₃₄N₄ = 690.83) 1-53 m/z = 738.28 (C₅₄H₃₄N₄ = 738.87) 1-54m/z = 814.31 (C₆₀H₃₈N₄ = 814.97) 1-55 m/z = 788.29 (C₅₈H₃₆N₄ = 788.93)1-56 m/z = 788.29 (C₅₈H₃₆N₄ = 788.93) 1-57 m/z = 662.25 (C₄₈H₃₀N₄ =662.78) 1-58 m/z = 738.28 (C₅₄H₃₄N₄ = 738.87) 1-59 m/z = 762.28(C₅₆H₃₄N₄ = 762.90) 1-60 m/z = 712.26 (C₅₂H₃₂N₄ = 712.84) 1-61 m/z =712.26 (C₅₂H₃₂N₄ = 712.84) 1-62 m/z = 738.28 (C₅₄H₃₄N₄ = 738.87) 1-63m/z = 778.31 (C₅₇H₃₈N₄ = 778.94) 1-64 m/z = 768.23 (C₅₄H₃₂N₄S = 768.92)1-65 m/z = 752.26 (C₅₄H₃₂N₄O = 752.86) 1-66 m/z = 768.23 (C₅₄H₃₂N₄S =768.92) 1-67 m/z = 752.26 (C₅₄H₃₂N₄O = 752.86) 1-68 m/z = 827.30(C₆₀H₃₇N₅ = 827.97) 1-69 m/z = 667.28 (C₄₈H₂₅D₅N₄ = 667.81) 1-70 m/z =788.29 (C₅₈H₃₆N₄ = 788.93) 1-71 m/z = 788.29 (C₅₈H₃₆N₄ = 788.93) 1-72m/z = 788.29 (C₅₈H₃₆N₄ = 788.93) 1-73 m/z = 788.29 (C₅₈H₃₆N₄ = 788.93)1-74 m/z = 712.26 (C₅₂H₃₂N₄ = 712.84) 1-75 m/z = 738.28 (C₅₄H₃₄N₄ =738.87) 1-76 m/z = 778.31 (C₅₇H₃₈N₄ = 778.94) 1-77 m/z = 739.27(C₅₃H₃₃N₅ = 739.86) 1-78 m/z = 664.26 (C₄₈H₃₂N₄ = 664.79) 1-79 m/z =726.28 (C₅₃H₃₄N₄ = 726.86) 1-80 m/z = 663.24 (C₄₇H₂₃N₅ = 663.77) 1-81m/z = 738.28 (C₅₄H₃₄N₄ = 738.87) 1-82 m/z = 738.28 (C₅₄H₃₄N₄ = 738.87)1-83 m/z = 788.29 (C₅₈H₃₆N₄ = 788.93) 1-84 m/z = 788.29 (C₅₈H₃₆N₄ =788.93) 1-85 m/z = 662.25 (C₄₈H₃₀N₄ = 662.78) 1-86 m/z = 738.28(C₅₄H₃₄N₄ = 738.87) 1-87 m/z = 762.28 (C₅₆H₃₄N₄ = 762.90) 1-88 m/z =712.26 (C₅₂H₃₂N₄ = 712.84) 1-89 m/z = 712.26 (C₅₂H₃₂N₄ = 712.84) 1-90m/z = 738.28 (C₅₄H₃₄N₄ = 738.87) 1-91 m/z = 778.31 (C₅₇H₃₈N₄ = 778.94)1-92 m/z = 768.23 (C₅₄H₃₂N₄S = 768.92) 1-93 m/z = 752.26 (C₅₄H₃₂N₄O =752.86) 1-94 m/z = 768.23 (C₅₄H₃₂N₄S = 768.92) 1-95 m/z = 752.26(C₅₄H₃₂N₄O = 752.86) 1-96 m/z = 827.30 (C₆₀H₃₇N₅ = 827.97) 1-97 m/z =667.28 (C₄₈H₂₅D₅N₄ = 667.81) 1-98 m/z = 788.29 (C₅₈H₃₆N₄ = 788.93) 1-99m/z = 788.29 (C₅₈H₃₆N₄ = 788.93) 1-100 m/z = 788.29 (C₅₈H₃₆N₄ = 788.93)1-101 m/z = 788.29 (C₅₈H₃₆N₄ = 788.93) 1-102 m/z = 712.26 (C₅₂H₃₂N₄ =712.84) 1-103 m/z = 738.28 (C₅₄H₃₄N₄ = 738.87) 1-104 m/z = 778.31(C₅₇H₃₈N₄ = 778.94) 1-105 m/z = 663.24 (C₄₇H₂₉N₅ = 663.77) 1-106 m/z =614.25 (C₄₄H₃₀N₄ = 614.74) 1-107 m/z = 738.28 (C₅₄H₃₄N₄ = 738.87) 1-108m/z = 814.31 (C₆₀H₃₈N₄ = 814.97) 1-109 m/z = 712.26 (C₅₂H₃₂N₄ = 712.84)1-110 m/z = 788.29 (C₅₈H₃₆N₄ = 788.93) 1-111 m/z = 762.28 (C₅₆H₃₄N₄ =762.90) 1-112 m/z = 788.29 (C₅₈H₃₆N₄ = 788.93) 1-113 m/z = 828.33(C₆₁H₄₀N₄ = 829.00) 1-114 m/z = 818.25 (C₅₈H₃₄N₄S = 818.98) 1-115 m/z =802.27 (C₅₈H₃₄N₄O = 802.92) 1-116 m/z = 877.32 (C₆₄H₃₉N₅ = 878.03) 1-117m/z = 762.28 (C₅₆H₃₄N₄ = 762.90) 1-118 m/z = 788.29 (C₅₈H₃₆N₄ = 788.93)1-119 m/z = 789.29 (C₅₇H₃₅N₅ = 789.92) 1-120 m/z = 838.31 (C₆₂H₃₈N₄ =838.99) 1-121 m/z = 712.26 (C₅₂H₃₂N₄ = 712.84) 1-122 m/z = 788.29(C₅₈H₃₆N₄ = 788.93) 1-123 m/z = 762.28 (C₅₆H₃₄N₄ = 762.90) 1-124 m/z =788.29 (C₅₈H₃₆N₄ = 788.93) 1-125 m/z = 828.33 (C₆₁H₄₀N₄ = 829.00) 1-126m/z = 802.27 (C₅₈H₃₄N₄O = 802.92) 1-127 m/z = 818.25 (C₅₈H₃₄N₄S =818.98) 1-128 m/z = 877.32 (C₆₄H₃₉N₅ = 878.03) 1-129 m/z = 762.28(C₅₆H₃₄N₄ = 762.90) 1-130 m/z = 788.29 (C₅₈H₃₆N₄ = 788.93) 1-131 m/z =788.29 (C₅₈H₃₆N₄ = 788.93) 1-132 m/z = 838.31 (C₆₂H₃₈N₄ = 838.99) 1-133m/z = 663.24 (C₄₇H₂₉N₅ = 663.77) 1-134 m/z = 663.24 (C₄₇H₂₉N₅ = 663.77)1-135 m/z = 739.27 (C₅₃H₃₃N₅ = 739.86) 1-136 m/z = 739.27 (C₅₃H₃₃N₅ =739.86) 1-137 m/z = 663.24 (C₄₇H₂₉N₅ = 663.77) 1-138 m/z = 663.24(C₄₇H₂₉N₅ = 663.77) 1-139 m/z = 713.26 (C₅₁H₃₁N₅ = 713.83) 1-140 m/z =713.26 (C₅₁H₃₁N₅ = 713.83) 1-141 m/z = 663.24 (C₄₇H₂₉N₅ = 663.77) 1-142m/z = 663.24 (C₄₇H₂₉N₅ = 663.77) 1-143 m/z = 713.26 (C₅₁H₃₁N₅ = 713.83)1-144 m/z = 713.26 (C₅₁H₃₁N₅ = 713.83) 1-145 m/z = 713.26 (C₅₁H₃₁N₅ =713.83) 1-146 m/z = 713.26 (C₅₁H₃₁N₅ = 713.83) 1-147 m/z = 739.27(C₅₃H₃₃N₅ = 739.86) 1-148 m/z = 739.27 (C₅₃H₃₃N₅ = 739.86) 2-1 m/z =662.25 (C₄₈H₃₀N₄ = 662.78) 2-2 m/z = 738.28 (C₅₄H₃₄N₄ = 738.87) 2-3 m/z= 762.28 (C₅₆H₃₄N₄ = 762.90) 2-4 m/z = 712.26 (C₅₂H₃₂N₄ = 712.84) 2-5m/z = 738.28 (C₅₄H₃₄N₄ = 738.87) 2-6 m/z = 778.31 (C₅₇H₃₈N₄ = 778.94)2-7 m/z = 768.23 (C₅₄H₃₂N₄S = 768.92) 2-8 m/z = 752.26 (C₅₄H₃₂N₄O =752.86) 2-9 m/z = 827.30 (C₆₀H₃₇N₅ = 827.97) 2-10 m/z = 788.29 (C₅₈H₃₆N₄= 788.93) 2-11 m/z = 788.29 (C₅₈H₃₆N₄ = 788.93) 2-12 m/z = 788.29(C₅₈H₃₆N₄ = 788.93) 2-13 m/z = 712.26 (C₅₂H₃₂N₄ = 712.84) 2-14 m/z =738.28 (C₅₄H₃₄N₄ = 738.87) 2-15 m/z = 778.31 (C₅₇H₃₈N₄ = 778.94) 2-16m/z = 739.27 (C₅₃H₃₃N₅ = 739.86) 2-17 m/z = 738.28 (C₅₄H₃₄N₄ = 738.87)2-18 m/z = 738.28 (C₅₄H₃₄N₄ = 738.87) 2-19 m/z = 788.29 (C₅₈H₃₆N₄ =788.93) 2-20 m/z = 788.29 (C₅₈H₃₆N₄ = 788.93) 2-21 m/z = 662.25(C₄₈H₃₀N₄ = 662.78) 2-22 m/z = 738.28 (C₅₄H₃₄N₄ = 738.87) 2-23 m/z =762.28 (C₅₆H₃₄N₄ = 762.90) 2-24 m/z = 712.26 (C₅₂H₃₂N₄ = 712.84) 2-25m/z = 738.28 (C₅₄H₃₄N₄ = 738.87) 2-26 m/z = 778.31 (C₅₇H₃₈N₄ = 778.94)2-27 m/z = 768.23 (C₅₄H₃₂N₄S = 768.92) 2-28 m/z = 752.26 (C₅₄H₃₂N₄O =752.86) 2-29 m/z = 827.30 (C₆₀H₃₇N₅ = 827.97) 2-30 m/z = 788.29(C₅₈H₃₆N₄ = 788.93) 2-31 m/z = 788.29 (C₅₈H₃₆N₄ = 788.93) 2-32 m/z =788.29 (C₅₈H₃₆N₄ = 788.93) 2-33 m/z = 712.26 (C₅₂H₃₂N₄ = 712.84) 2-34m/z = 738.28 (C₅₄H₃₄N₄ = 738.87) 2-35 m/z = 778.31 (C₅₇H₃₈N₄ = 778.94)2-36 m/z = 739.27 (C₅₃H₃₃N₅ = 739.86) 2-37 m/z = 738.28 (C₅₄H₃₄N₄ =738.87) 2-38 m/z = 738.28 (C₅₄H₃₄N₄ = 738.87) 2-39 m/z = 788.29(C₅₈H₃₆N₄ = 788.93) 2-40 m/z = 788.29 (C₅₈H₃₆N₄ = 788.93) 2-41 m/z =662.25 (C₄₈H₃₀N₄ = 662.78) 2-42 m/z = 738.28 (C₅₄H₃₄N₄ = 738.87) 2-43m/z = 762.28 (C₅₆H₃₄N₄ = 762.90) 2-44 m/z = 712.26 (C₅₂H₃₂N₄ = 712.84)2-45 m/z = 738.28 (C₅₄H₃₄N₄ = 738.87) 2-46 m/z = 778.31 (C₅₇H₃₈N₄ =778.94) 2-47 m/z = 768.23 (C₅₄H₃₂N₄S = 768.92) 2-48 m/z = 752.26(C₅₄H₃₂N₄O = 752.86) 2-49 m/z = 827.30 (C₆₀H₃₇N₅ = 827.97) 2-50 m/z =788.29 (C₅₈H₃₆N₄ = 788.93) 2-51 m/z = 788.29 (C₅₈H₃₆N₄ = 788.93) 2-52m/z = 788.29 (C₅₈H₃₆N₄ = 788.93) 2-53 m/z = 712.26 (C₅₂H₃₂N₄ = 712.84)2-54 m/z = 738.28 (C₅₄H₃₄N₄ = 738.87) 2-55 m/z = 778.31 (C₅₇H₃₈N₄ =778.94) 2-56 m/z = 663.24 (C₄₇H₂₉N₅ = 663.77) 2-57 m/z = 738.28(C₅₄H₃₄N₄ = 738.87) 2-58 m/z = 738.28 (C₅₄H₃₄N₄ = 738.87) 2-59 m/z =788.29 (C₅₈H₃₆N₄ = 788.93) 2-60 m/z = 788.29 (C₅₈H₃₆N₄ = 788.93) 2-61m/z = 662.25 (C₄₈H₃₀N₄ = 662.78) 2-62 m/z = 738.28 (C₅₄H₃₄N₄ = 738.87)2-63 m/z = 762.28 (C₅₆H₃₄N₄ = 762.90) 2-64 m/z = 712.26 (C₅₂H₃₂N₄ =712.84) 2-65 m/z = 738.28 (C₅₄H₃₄N₄ = 738.87) 2-66 m/z = 778.31(C₅₇H₃₈N₄ = 778.94) 2-67 m/z = 768.23 (C₅₄H₃₂N₄S = 768.92) 2-68 m/z =752.26 (C₅₄H₃₂N₄O = 752.86) 2-69 m/z = 827.30 (C₆₀H₃₇N₅ = 827.97) 2-70m/z = 788.29 (C₅₈H₃₆N₄ = 788.93) 2-71 m/z = 788.29 (C₅₈H₃₆N₄ = 788.93)2-72 m/z = 788.29 (C₅₈H₃₆N₄ = 788.93) 2-73 m/z = 712.26 (C₅₂H₃₂N₄ =712.84) 2-74 m/z = 738.28 (C₅₄H₃₄N₄ = 738.87) 2-75 m/z = 778.31(C₅₇H₃₈N₄ = 778.94) 2-76 m/z = 739.27 (C₅₃H₃₃N₅ = 739.86) 2-77 m/z =738.28 (C₅₄H₃₄N₄ = 738.87) 2-78 m/z = 738.28 (C₅₄H₃₄N₄ = 738.87) 2-79m/z = 788.29 (C₅₈H₃₆N₄ = 788.93) 2-80 m/z = 788.29 (C₅₈H₃₆N₄ = 788.93)2-81 m/z = 712.26 (C₅₂H₃₂N₄ = 712.84) 2-82 m/z = 788.29 (C₅₈H₃₆N₄ =788.93) 2-83 m/z = 762.28 (C₅₆H₃₄N₄ = 762.90) 2-84 m/z = 788.29(C₅₈H₃₆N₄ = 788.93) 2-85 m/z = 828.33 (C₆₁H₄₀N₄ = 829.00) 2-86 m/z =818.25 (C₅₈H₃₄N₄S = 818.98) 2-87 m/z = 802.27 (C₅₈H₃₄N₄O = 802.92) 2-88m/z = 877.32 (C₆₄H₃₉N₅ = 878.03) 2-89 m/z = 762.28 (C₅₆H₃₄N₄ = 762.90)2-90 m/z = 788.29 (C₅₈H₃₆N₄ = 788.93) 2-91 m/z = 789.29 (C₅₇H₃₅N₅ =789.92) 2-92 m/z = 838.31 (C₆₂H₃₈N₄ = 838.99) 2-93 m/z = 712.26(C₅₂H₃₂N₄ = 712.84) 2-94 m/z = 788.29 (C₅₈H₃₆N₄ = 788.93) 2-95 m/z =762.28 (C₅₆H₃₄N₄ = 762.90) 2-96 m/z = 788.29 (C₅₈H₃₆N₄ = 788.93) 2-97m/z = 828.33 (C₆₁H₄₀N₄ = 829.00) 2-98 m/z = 802.27 (C₅₈H₃₄N₄O = 802.92)2-99 m/z = 818.25 (C₅₈H₃₄N₄S = 818.98) 2-100 m/z = 877.32 (C₆₄H₃₉N₅ =878.03) 2-101 m/z = 762.28 (C₅₆H₃₄N₄ = 762.90) 2-102 m/z = 788.29(C₅₈H₃₆N₄ = 788.93) 2-103 m/z = 788.29 (C₅₈H₃₆N₄ = 788.93) 2-104 m/z =838.31 (C₆₂H₃₈N₄ = 838.99) 2-105 m/z = 663.24 (C₄₇H₂₉N₅ = 663.77) 2-106m/z = 663.24 (C₄₇H₂₉N₅ = 663.77) 2-107 m/z = 739.27 (C₅₃H₃₃N₅ = 739.86)2-108 m/z = 739.27 (C₅₃H₃₃N₅ = 739.86) 2-109 m/z = 663.24 (C₄₇H₂₉N₅ =663.77) 2-110 m/z = 663.24 (C₄₇H₂₉N₅ = 663.77) 2-111 m/z = 713.26(C₅₁H₃₁N₅ = 713.83) 2-112 m/z = 713.26 (C₅₁H₃₁N₅ = 713.83) 2-113 m/z =663.24 (C₄₇H₂₉N₅ = 663.77) 2-114 m/z = 663.24 (C₄₇H₂₉N₅ = 663.77) 2-115m/z = 713.26 (C₅₁H₃₁N₅ = 713.83) 2-116 m/z = 713.26 (C₅₁H₃₁N₅ = 713.83)2-117 m/z = 713.26 (C₅₁H₃₁N₅ = 713.83) 2-118 m/z = 713.26 (C₅₁H₃₁N₅ =713.83) 2-119 m/z = 739.27 (C₅₃H₃₃N₅ = 739.86) 2-120 m/z = 739.27(C₅₃H₃₃N₅ = 739.86)

Meanwhile, the synthesis examples of the present invention, representedby Formula 1, have been described, but these are based on a Suzukicross-coupling reaction, a Bromination reaction, an Ullmann reaction, aMiyaura boration reaction, and a Buchwald-Hartwig cross couplingreaction. A person skilled in the art could easily understand that theabove reactions proceed even though, besides the substituents specifiedin the specific synthesis examples, the other substituents (substituentsof Ar₁ to Ar₂, L, X₁ to X₄, and R′) defined in Formula 1 are bonded. Forexample, all of the reactions of the starting material→M 1-I, a startingmaterial→M 2-I, Sub 1-III→Sub 1-IV, Sub 1-V→Sub 1, in Reaction Scheme 2,and the reaction of the starting material→Sub 2 in Reaction Scheme 10are based on the Suzuki cross-coupling reaction; the reaction of M1-II→Sub 1-I in Reaction Scheme 2 is based on the Bromination reaction;the reaction of Sub 1-I→Sub 1-II in Reaction Scheme 2 is based on theUllmann reaction; the reactions of Sub 1-II→Sub 1-III and Sub 1-IV→Sub1-V are based on the Miyaura boration reaction. The reaction schemes forproduct synthesis (Reaction Schemes 17 to 26) are based on theBuchwald-Hartwig cross coupling reaction, and the above reactions willproceed even though substituents that are not specified therein arebonded.

Manufacture and Evaluation of Organic electronic Element

Example 1: Light Emitting Layer (Phosphorescent Red Host)

An organic light emitting diode was manufactured according to a normalmethod by using the inventive compounds obtained through synthesis as ahost material of a light emitting layer.

First, an ITO layer (anode) was formed on a glass substrate, and then afilm of 4,4′,4″-Tris[2-naphthyl(phenyl)amino]triphenylamine(hereinafter, abbreviated as 2-TNATA) was vacuum-deposited on the ITOlayer to form a hole injection layer with a thickness of 60 nm.Subsequently, a film then a film of4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter, abbreviatedas NPD) was vacuum-deposited with a thickness of 20 nm on the holeinjection layer to form a hole transport layer. Then, a light emittinglayer with a thickness of 30 nm was deposited on the hole transportlayer by doping the hole transport layer with the inventive compound asa host material and (piq)₂Ir(acac) [bis-(1-phenylisoquinolyl)iridium(III) acetylacetonate] as a dopant material at a weight ratio of95:5. Then, a film of(1,1′-bisphenyl)-4-olato)bis(2-methyl-8-quinolinolato)aluminum(hereinafter abbreviated as “BAlq”) was vacuum-deposited with athickness of 10 nm on the light emitting layer to forma hole blockinglayer, and a film of tris(8-quinolinolato)aluminum (hereinafterabbreviated as “Alq₃”) was formed with a thickness of 40 nm on the holeblocking layer to form an electron transport layer. Thereafter, LiF ashalogenated alkali metal was deposited with a thickness of 0.2 nm toform an electron injection layer, and then Al was deposited with athickness of 150 nm to form a negative electrode. In this way, anorganic light emitting diode was manufactured.

Example 2 to EXAMPLE 268 Light Emitting Layer (Phosphorescent Red Host)

Organic light emitting diodes were manufactured by the same method as inExample 1 except that Compounds 1-2 to 1-148 and 2-1 to 2-120 listed intable 4, instead of inventive compound 1-1, were used as a host materialof the light emitting layer.

Comparative Example 1

An organic light emitting diode was manufactured by the same method asin Example 1 except that comparative compound 1 below, instead ofinventive compound 1-1, was used as a host material of the lightemitting layer.

Comparative Compound 1

bis(10-hydroxybenzo[h] qinolinato) beryllium (hereinafter, abbreviatedas “Bebq2”)

Comparative Example 2

An organic light emitting diode was manufactured by the same method asin Example 1 except that comparative compound 2 below, instead ofinventive compound 1-1, was used as a host material of the lightemitting layer.

Comparative Compound 2

Comparative Example 3

An organic light emitting diode was manufactured by the same method asin Example 1 except that comparative compound 3 below, instead ofinventive compound 1-1, was used as a host material of the lightemitting layer.

Comparative Compound 3

Comparative Example 4

An organic light emitting diode was manufactured by the same method asin Example 1 except that comparative compound 4 below, instead ofinventive compound 1-1, was used as a host material of the lightemitting layer.

Comparative Compound 4

Comparative Example 5

An organic light emitting diode was manufactured by the same method asin Example 1 except that comparative compound 5 below, instead ofinventive compound 1-1, was used as a host material of the lightemitting layer.

Comparative Compound 5

Comparative Example 6

An organic light emitting diode was manufactured by the same method asin Example 1 except that comparative compound 6 below, instead ofinventive compound 1-1, was used as a host material of the lightemitting layer.

Comparative Compound 6

Comparative Example 7

An organic light emitting diode was manufactured by the same method asin Example 1 except that comparative compound 7 below, instead ofinventive compound 1-1, was used as a host material of the lightemitting layer.

Comparative Compound 7

A forward bias DC voltage was applied to each of the thus manufacturedorganic light emitting diodes of Examples 1 to 268 and ComparativeExamples 1 to 7, and electroluminescent (EL) characteristics thereofwere measured by PR-650 from Photoresearch Company. Also, T95 lifespanwas measured by lifespan measuring equipment from Mcscience Company at areference brightness of 300 cd/m². The measurement results are shown inTable 4.

TABLE 4 Current Voltage Density Brightness Efficiency Lifetime CIECompound (V) (mA/cm²) (cd/m²) (cd/A) T(90) x y Comp. Ex. (1) Comp. Com.1 5.8 6.0 300.0 5.0 89.8 0.66 0.33 Comp. Ex. (2) Comp. com. 2 5.9 5.6300.0 5.4 95.3 0.66 0.33 Comp. Ex. (3) Comp. com. 3 5.6 5.3 300.0 5.794.7 0.66 0.34 Comp. Ex. (4) Comp. com. 4 5.6 5.5 300.0 5.5 90.2 0.660.33 Comp. Ex. (5) Comp. com. 5 5.3 4.8 300.0 6.2 98.1 0.66 0.33 Comp.Ex. (6) Comp. com. 6 5.4 4.9 300.0 6.1 96.4 0.66 0.34 Comp. Ex. (7)Comp. com. 7 5.9 5.8 300.0 5.2 82.2 0.66 0.34 Ex. (1) Com. (1-1) 5.2 3.3300.0 9.0 145.9 0.66 0.34 Ex. (2) Com. (1-2) 5.3 3.4 300.0 8.7 131.30.66 0.33 Ex. (3) Com. (1-3) 5.4 3.6 300.0 8.3 126.5 0.66 0.33 Ex. (4)Com. (1-4) 5.3 3.3 300.0 9.0 148.1 0.66 0.34 Ex. (5) Com. (1-5) 5.2 3.3300.0 9.0 141.3 0.66 0.33 Ex. (6) Com. (1-6) 5.2 3.6 300.0 8.3 125.10.66 0.33 Ex. (7) Com. (1-7) 5.3 3.5 300.0 8.6 124.3 0.66 0.33 Ex. (8)Com. (1-8) 5.2 3.4 300.0 8.7 124.0 0.66 0.33 Ex. (9) Com. (1-9) 5.4 3.6300.0 8.4 126.8 0.66 0.33 Ex. (10) Com. (1-10) 5.3 3.5 300.0 8.6 127.20.66 0.33 Ex. (11) Com. (1-11) 5.3 3.5 300.0 8.6 128.3 0.66 0.34 Ex.(12) Com. (1-12) 5.3 3.5 300.0 8.6 127.9 0.66 0.34 Ex. (13) Com. (1-13)5.2 3.5 300.0 8.6 127.8 0.66 0.34 Ex. (14) Com. (1-14) 5.2 3.5 300.0 8.6123.6 0.66 0.33 Ex. (15) Com. (1-15) 5.4 3.5 300.0 8.5 125.7 0.66 0.34Ex. (16) Com. (1-16) 5.4 3.5 300.0 8.5 123.9 0.66 0.33 Ex. (17) Com.(1-17) 5.3 3.4 300.0 8.7 128.4 0.66 0.33 Ex. (18) Com. (1-18) 5.3 3.4300.0 8.8 132.7 0.66 0.33 Ex. (19) Com. (1-19) 5.2 3.4 300.0 8.9 133.20.66 0.34 Ex. (20) Com. (1-20) 5.3 3.7 300.0 8.1 126.3 0.66 0.34 Ex.(21) Com. (1-21) 5.4 3.6 300.0 8.4 126.4 0.66 0.33 Ex. (22) Com. (1-22)5.5 3.8 300.0 7.9 125.7 0.66 0.34 Ex. (23) Com. (1-23) 5.3 3.8 300.0 8.0125.0 0.66 0.33 Ex. (24) Com. (1-24) 5.3 3.8 300.0 7.9 124.1 0.66 0.34Ex. (25) Com. (1-25) 5.4 3.8 300.0 7.8 123.8 0.66 0.33 Ex. (26) Com.(1-26) 5.4 3.7 300.0 8.2 125.6 0.66 0.34 Ex. (27) Com. (1-27) 5.4 3.7300.0 8.1 124.5 0.66 0.33 Ex. (28) Com. (1-28) 5.5 3.8 300.0 7.9 124.20.66 0.33 Ex. (29) Com. (1-29) 5.3 3.4 300.0 8.7 135.6 0.66 0.34 Ex.(30) Com. (1-30) 5.3 3.5 300.0 8.6 123.8 0.66 0.34 Ex. (31) Com. (1-31)5.3 3.6 300.0 8.4 126.5 0.66 0.33 Ex. (32) Com. (1-32) 5.2 3.4 300.0 8.7129.6 0.66 0.33 Ex. (33) Com. (1-33) 5.3 3.4 300.0 8.9 134.4 0.66 0.33Ex. (34) Com. (1-34) 5.2 3.7 300.0 8.2 124.0 0.66 0.34 Ex. (35) Com.(1-35) 5.3 3.5 300.0 8.5 126.9 0.66 0.33 Ex. (36) Com. (1-36) 5.3 3.7300.0 8.1 127.7 0.66 0.33 Ex. (37) Com. (1-37) 5.3 3.7 300.0 8.1 126.80.66 0.33 Ex. (38) Com. (1-38) 5.2 3.5 300.0 8.6 127.1 0.66 0.33 Ex.(39) Com. (1-39) 5.4 3.7 300.0 8.2 127.9 0.66 0.33 Ex. (40) Com. (1-40)5.3 3.5 300.0 8.5 126.6 0.66 0.33 Ex. (41) Com. (1-41) 5.2 3.6 300.0 8.4128.7 0.66 0.33 Ex. (42) Com. (1-42) 5.3 3.7 300.0 8.2 124.0 0.66 0.34Ex. (43) Com. (1-43) 5.4 3.6 300.0 8.3 126.7 0.66 0.33 Ex. (44) Com.(1-44) 5.4 3.6 300.0 8.3 127.1 0.66 0.33 Ex. (45) Com. (1-45) 5.3 3.7300.0 8.2 126.5 0.66 0.33 Ex. (46) Com. (1-46) 5.3 3.5 300.0 8.5 124.10.66 0.34 Ex. (47) Com. (1-47) 5.2 3.5 300.0 8.6 126.3 0.66 0.34 Ex.(48) Com. (1-48) 5.5 3.7 300.0 8.1 123.9 0.66 0.33 Ex. (49) Com. (1-49)5.4 4.0 300.0 7.5 126.6 0.66 0.33 Ex. (50) Com. (1-50) 5.4 3.8 300.0 7.9126.0 0.66 0.34 Ex. (51) Com. (1-51) 5.3 4.0 300.0 7.5 125.8 0.66 0.34Ex. (52) Com. (1-52) 5.3 3.9 300.0 7.7 126.6 0.66 0.34 Ex. (53) Com.(1-53) 5.4 3.8 300.0 7.8 127.9 0.66 0.34 Ex. (54) Com. (1-54) 5.5 3.8300.0 7.9 126.5 0.66 0.34 Ex. (55) Com. (1-55) 5.4 4.0 300.0 7.5 127.10.66 0.33 Ex. (56) Com. (1-56) 5.4 3.8 300.0 7.9 127.5 0.66 0.34 Ex.(57) Com. (1-57) 5.2 3.3 300.0 9.1 153.9 0.66 0.34 Ex. (58) Com. (1-58)5.2 3.3 300.0 9.1 139.4 0.66 0.34 Ex. (59) Com. (1-59) 5.2 3.4 300.0 8.9132.2 0.66 0.33 Ex. (60) Com. (1-60) 5.2 3.2 300.0 9.3 150.3 0.66 0.34Ex. (61) Com. (1-61) 5.2 3.3 300.0 9.1 153.2 0.66 0.34 Ex. (62) Com.(1-62) 5.3 3.5 300.0 8.5 129.7 0.66 0.34 Ex. (63) Com. (1-63) 5.2 3.5300.0 8.5 130.8 0.66 0.34 Ex. (64) Com. (1-64) 5.2 3.3 300.0 9.0 136.60.66 0.33 Ex. (65) Com. (1-65) 5.2 3.4 300.0 8.8 134.8 0.66 0.34 Ex.(66) Com. (1-66) 5.2 3.4 300.0 8.8 130.9 0.66 0.34 Ex. (67) Com. (1-67)5.2 3.4 300.0 8.9 126.4 0.66 0.33 Ex. (68) Com. (1-68) 5.2 3.5 300.0 8.6133.1 0.66 0.34 Ex. (69) Com. (1-69) 5.2 3.4 300.0 8.8 126.3 0.66 0.33Ex. (70) Com. (1-70) 5.3 3.4 300.0 8.9 127.6 0.66 0.33 Ex. (71) Com.(1-71) 5.3 3.4 300.0 8.9 132.9 0.66 0.34 Ex. (72) Com. (1-72) 5.2 3.5300.0 8.5 138.7 0.66 0.33 Ex. (73) Com. (1-73) 5.3 3.5 300.0 8.6 124.50.66 0.34 Ex. (74) Com. (1-74) 5.3 3.3 300.0 9.0 145.3 0.66 0.33 Ex.(75) Com. (1-75) 5.2 3.3 300.0 9.0 141.4 0.66 0.33 Ex. (76) Com. (1-76)5.4 3.8 300.0 8.0 124.3 0.66 0.34 Ex. (77) Com. (1-77) 5.3 3.5 300.0 8.5125.9 0.66 0.33 Ex. (78) Com. (1-78) 5.3 3.6 300.0 8.4 123.9 0.66 0.34Ex. (79) Com. (1-79) 5.3 3.6 300.0 8.3 128.6 0.66 0.33 Ex. (80) Com.(1-80) 5.3 3.5 300.0 8.5 127.9 0.66 0.34 Ex. (81) Com. (1-81) 5.3 3.7300.0 8.1 127.3 0.66 0.33 Ex. (82) Com. (1-82) 5.4 3.7 300.0 8.2 124.10.66 0.34 Ex. (83) Com. (1-83) 5.3 3.7 300.0 8.1 125.9 0.66 0.34 Ex.(84) Com. (1-84) 5.2 3.7 300.0 8.2 126.2 0.66 0.34 Ex. (85) Com. (1-85)5.2 3.3 300.0 9.0 145.1 0.66 0.33 Ex. (86) Com. (1-86) 5.3 3.4 300.0 8.7131.9 0.66 0.33 Ex. (87) Com. (1-87) 5.2 3.5 300.0 8.6 124.5 0.66 0.33Ex. (88) Com. (1-88) 5.3 3.3 300.0 9.0 143.1 0.66 0.33 Ex. (89) Com.(1-89) 5.2 3.4 300.0 8.9 143.6 0.66 0.34 Ex. (90) Com. (1-90) 5.2 3.5300.0 8.6 126.0 0.66 0.34 Ex. (91) Com. (1-91) 5.2 3.4 300.0 8.8 128.40.66 0.33 Ex. (92) Com. (1-92) 5.3 3.4 300.0 8.8 125.6 0.66 0.34 Ex.(93) Com. (1-93) 5.2 3.6 300.0 8.4 125.6 0.66 0.34 Ex. (94) Com. (1-94)5.3 3.4 300.0 8.7 125.0 0.66 0.34 Ex. (95) Com. (1-95) 5.3 3.5 300.0 8.5124.6 0.66 0.34 Ex. (96) Com. (1-96) 5.3 3.6 300.0 8.3 124.8 0.66 0.33Ex. (97) Com. (1-97) 5.2 3.5 300.0 8.6 127.9 0.66 0.34 Ex. (98) Com.(1-98) 5.2 3.5 300.0 8.6 125.7 0.66 0.34 Ex. (99) Com. (1-99) 5.2 3.6300.0 8.4 126.5 0.66 0.33 Ex. (100) Com. (1-100) 5.3 3.5 300.0 8.5 126.40.66 0.34 Ex. (101) Com. (1-101) 5.3 3.5 300.0 8.6 127.8 0.66 0.34 Ex.(102) Com. (1-102) 5.2 3.4 300.0 8.8 133.3 0.66 0.33 Ex. (103) Com.(1-103) 5.3 3.6 300.0 8.4 127.3 0.66 0.33 Ex. (104) Com. (1-104) 5.2 3.8300.0 7.8 124.2 0.66 0.34 Ex. (105) Com. (1-105) 5.3 3.8 300.0 8.0 125.10.66 0.33 Ex. (106) Com. (1-106) 5.2 3.7 300.0 8.1 125.8 0.66 0.33 Ex.(107) Com. (1-107) 5.4 3.9 300.0 7.7 124.6 0.66 0.34 Ex. (108) Com.(1-108) 5.4 3.6 300.0 8.3 127.5 0.66 0.34 Ex. (109) Com. (1-109) 5.3 3.5300.0 8.5 137.0 0.66 0.34 Ex. (110) Com. (1-110) 5.2 3.6 300.0 8.4 127.80.66 0.33 Ex. (111) Com. (1-111) 5.3 3.5 300.0 8.6 132.0 0.66 0.33 Ex.(112) Com. (1-112) 5.4 3.6 300.0 8.3 126.0 0.66 0.34 Ex. (113) Com.(1-113) 5.4 3.7 300.0 8.1 126.1 0.66 0.33 Ex. (114) Com. (1-114) 5.4 3.7300.0 8.2 124.6 0.66 0.34 Ex. (115) Com. (1-115) 5.3 3.8 300.0 8.0 128.70.66 0.34 Ex. (116) Com. (1-116) 5.3 3.8 300.0 8.0 127.2 0.66 0.33 Ex.(117) Com. (1-117) 5.5 3.6 300.0 8.4 127.3 0.66 0.34 Ex. (118) Com.(1-118) 5.5 3.6 300.0 8.4 124.6 0.66 0.33 Ex. (119) Com. (1-119) 5.5 4.0300.0 7.5 124.8 0.66 0.34 Ex. (120) Com. (1-120) 5.5 3.9 300.0 7.7 126.80.66 0.33 Ex. (121) Com. (1-121) 5.2 3.5 300.0 8.6 135.1 0.66 0.34 Ex.(122) Com. (1-122) 5.3 3.5 300.0 8.5 125.1 0.66 0.33 Ex. (123) Com.(1-123) 5.3 3.5 300.0 8.5 134.2 0.66 0.33 Ex. (124) Com. (1-124) 5.3 3.7300.0 8.1 126.9 0.66 0.34 Ex. (125) Com. (1-125) 5.3 3.7 300.0 8.1 124.00.66 0.33 Ex. (126) Com. (1-126) 5.5 3.7 300.0 8.1 128.1 0.66 0.33 Ex.(127) Com. (1-127) 5.4 3.6 300.0 8.4 125.2 0.66 0.34 Ex. (128) Com.(1-128) 5.3 3.8 300.0 8.0 126.7 0.66 0.33 Ex. (129) Com. (1-129) 5.4 3.5300.0 8.5 126.9 0.66 0.34 Ex. (130) Com. (1-130) 5.5 3.6 300.0 8.4 127.70.66 0.33 Ex. (131) Com. (1-131) 5.5 4.0 300.0 7.5 125.6 0.66 0.34 Ex.(132) Com. (1-132) 5.5 3.8 300.0 7.8 123.9 0.66 0.33 Ex. (133) Com.(1-133) 5.3 3.4 300.0 8.8 136.5 0.66 0.33 Ex. (134) Com. (1-134) 5.3 3.4300.0 8.8 129.1 0.66 0.33 Ex. (135) Com. (1-135) 5.3 3.5 300.0 8.5 123.60.66 0.33 Ex. (136) Com. (1-136) 5.2 3.6 300.0 8.3 124.8 0.66 0.34 Ex.(137) Com. (1-137) 5.2 3.5 300.0 8.6 124.4 0.66 0.33 Ex. (138) Com.(1-138) 5.3 3.5 300.0 8.5 125.9 0.66 0.33 Ex. (139) Com. (1-139) 5.3 3.3300.0 9.1 149.2 0.66 0.34 Ex. (140) Com. (1-140) 5.2 3.3 300.0 9.0 139.40.66 0.34 Ex. (141) Com. (1-141) 5.2 3.4 300.0 8.8 131.3 0.66 0.33 Ex.(142) Com. (1-142) 5.3 3.4 300.0 8.9 129.3 0.66 0.34 Ex. (143) Com.(1-143) 5.5 3.5 300.0 8.5 123.9 0.66 0.33 Ex. (144) Com. (1-144) 5.5 3.6300.0 8.4 125.5 0.66 0.33 Ex. (145) Com. (1-145) 5.4 3.6 300.0 8.4 124.70.66 0.33 Ex. (146) Com. (1-146) 5.5 3.5 300.0 8.5 125.7 0.66 0.33 Ex.(147) Com. (1-147) 5.3 3.6 300.0 8.4 126.4 0.66 0.34 Ex. (148) Com.(1-148) 5.5 3.8 300.0 8.0 128.4 0.66 0.34 Ex. (149) Com. (2-1) 5.3 3.4300.0 8.9 134.8 0.66 0.33 Ex. (150) Com. (2-2) 5.2 3.5 300.0 8.5 124.10.66 0.33 Ex. (151) Com. (2-3) 5.3 3.6 300.0 8.4 128.1 0.66 0.34 Ex.(152) Com. (2-4) 5.2 3.5 300.0 8.8 130.8 0.66 0.34 Ex. (153) Com. (2-5)5.2 3.7 300.0 8.1 127.3 0.66 0.34 Ex. (154) Com. (2-6) 5.3 3.6 300.0 8.4125.1 0.66 0.34 Ex. (155) Com. (2-7) 5.3 3.7 300.0 8.2 124.8 0.66 0.34Ex. (156) Com. (2-8) 5.3 3.5 300.0 8.6 125.0 0.66 0.33 Ex. (157) Com.(2-9) 5.2 3.5 300.0 8.6 124.7 0.66 0.33 Ex. (158) Com. (2-10) 5.4 3.5300.0 8.5 126.4 0.66 0.33 Ex. (159) Com. (2-11) 5.3 3.5 300.0 8.5 126.90.66 0.34 Ex. (160) Com. (2-12) 5.2 3.7 300.0 8.2 127.3 0.66 0.33 Ex.(161) Com. (2-13) 5.2 3.5 300.0 8.5 126.3 0.66 0.34 Ex. (162) Com.(2-14) 5.4 3.5 300.0 8.6 124.0 0.66 0.34 Ex. (163) Com. (2-15) 5.4 3.9300.0 7.6 126.5 0.66 0.34 Ex. (164) Com. (2-16) 5.5 3.8 300.0 8.0 127.30.66 0.33 Ex. (165) Com. (2-17) 5.4 3.9 300.0 7.7 126.8 0.66 0.34 Ex.(166) Com. (2-18) 5.3 4.0 300.0 7.5 128.6 0.66 0.33 Ex. (167) Com.(2-19) 5.5 3.8 300.0 7.8 127.2 0.66 0.34 Ex. (168) Com. (2-20) 5.4 3.7300.0 8.1 125.9 0.66 0.34 Ex. (169) Com. (2-21) 5.2 3.5 300.0 8.6 138.40.66 0.34 Ex. (170) Com. (2-22) 5.2 3.6 300.0 8.4 127.3 0.66 0.34 Ex.(171) Com. (2-23) 5.3 3.8 300.0 8.0 124.7 0.66 0.33 Ex. (172) Com.(2-24) 5.3 3.5 300.0 8.6 129.2 0.66 0.34 Ex. (173) Com. (2-25) 5.3 3.7300.0 8.1 127.4 0.66 0.34 Ex. (174) Com. (2-26) 5.2 3.8 300.0 7.9 128.00.66 0.34 Ex. (175) Com. (2-27) 5.3 3.6 300.0 8.4 124.9 0.66 0.34 Ex.(176) Com. (2-28) 5.3 3.7 300.0 8.2 125.9 0.66 0.34 Ex. (177) Com.(2-29) 5.3 3.6 300.0 8.3 128.1 0.66 0.33 Ex. (178) Com. (2-30) 5.3 3.6300.0 8.3 124.6 0.66 0.33 Ex. (179) Com. (2-31) 5.3 3.8 300.0 7.9 125.40.66 0.33 Ex. (180) Com. (2-32) 5.4 3.7 300.0 8.2 127.3 0.66 0.33 Ex.(181) Com. (2-33) 5.3 3.6 300.0 8.3 127.7 0.66 0.33 Ex. (182) Com.(2-34) 5.3 3.6 300.0 8.3 125.9 0.66 0.33 Ex. (183) Com. (2-35) 5.5 3.8300.0 7.9 126.7 0.66 0.34 Ex. (184) Com. (2-36) 5.5 3.8 300.0 7.8 124.10.66 0.34 Ex. (185) Com. (2-37) 5.4 3.8 300.0 7.8 127.7 0.66 0.34 Ex.(186) Com. (2-38) 5.5 3.9 300.0 7.6 123.6 0.66 0.34 Ex. (187) Com.(2-39) 5.5 3.8 300.0 7.8 123.9 0.66 0.34 Ex. (188) Com. (2-40) 5.3 3.9300.0 7.7 125.5 0.66 0.33 Ex. (189) Com. (2-41) 5.2 3.3 300.0 9.0 147.80.66 0.34 Ex. (190) Com. (2-42) 5.2 3.4 300.0 8.8 133.0 0.66 0.33 Ex.(191) Com. (2-43) 5.2 3.6 300.0 8.3 125.0 0.66 0.33 Ex. (192) Com.(2-44) 5.2 3.4 300.0 8.9 145.9 0.66 0.34 Ex. (193) Com. (2-45) 5.3 3.4300.0 8.7 126.9 0.66 0.33 Ex. (194) Com. (2-46) 5.3 3.6 300.0 8.4 127.70.66 0.34 Ex. (195) Com. (2-47) 5.3 3.6 300.0 8.4 128.0 0.66 0.34 Ex.(196) Com. (2-48) 5.3 3.5 300.0 8.5 127.3 0.66 0.33 Ex. (197) Com.(2-49) 5.3 3.6 300.0 8.4 125.7 0.66 0.34 Ex. (198) Com. (2-50) 5.3 3.5300.0 8.6 126.8 0.66 0.34 Ex. (199) Com. (2-51) 5.3 3.5 300.0 8.6 126.20.66 0.33 Ex. (200) Com. (2-52) 5.3 3.6 300.0 8.4 125.3 0.66 0.33 Ex.(201) Com. (2-53) 5.3 3.4 300.0 8.7 130.6 0.66 0.33 Ex. (202) Com.(2-54) 5.2 3.4 300.0 8.7 131.9 0.66 0.34 Ex. (203) Com. (2-55) 5.2 3.7300.0 8.2 127.5 0.66 0.33 Ex. (204) Com. (2-56) 5.3 3.6 300.0 8.3 128.00.66 0.34 Ex. (205) Com. (2-57) 5.3 3.7 300.0 8.2 123.7 0.66 0.34 Ex.(206) Com. (2-58) 5.5 3.7 300.0 8.2 124.5 0.66 0.34 Ex. (207) Com.(2-59) 5.4 3.7 300.0 8.2 124.9 0.66 0.33 Ex. (208) Com. (2-60) 5.4 3.8300.0 8.0 126.7 0.66 0.34 Ex. (209) Com. (2-61) 5.3 3.4 300.0 8.8 135.30.66 0.34 Ex. (210) Com. (2-62) 5.2 3.5 300.0 8.5 126.7 0.66 0.34 Ex.(211) Com. (2-63) 5.2 3.6 300.0 8.4 128.6 0.66 0.33 Ex. (212) Com.(2-64) 5.3 3.4 300.0 8.8 137.3 0.66 0.34 Ex. (213) Com. (2-65) 5.3 3.7300.0 8.2 124.9 0.66 0.34 Ex. (214) Com. (2-66) 5.2 3.5 300.0 8.5 126.50.66 0.34 Ex. (215) Com. (2-67) 5.2 3.5 300.0 8.6 127.3 0.66 0.34 Ex.(216) Com. (2-68) 5.2 3.5 300.0 8.5 124.1 0.66 0.34 Ex. (217) Com.(2-69) 5.3 3.6 300.0 8.3 125.6 0.66 0.34 Ex. (218) Com. (2-70) 5.2 3.6300.0 8.4 126.1 0.66 0.33 Ex. (219) Com. (2-71) 5.2 3.6 300.0 8.4 127.90.66 0.33 Ex. (220) Com. (2-72) 5.2 3.5 300.0 8.5 126.4 0.66 0.34 Ex.(221) Com. (2-73) 5.3 3.4 300.0 8.7 124.5 0.66 0.34 Ex. (222) Com.(2-74) 5.3 3.5 300.0 8.6 123.9 0.66 0.34 Ex. (223) Com. (2-75) 5.5 3.9300.0 7.6 125.0 0.66 0.34 Ex. (224) Com. (2-76) 5.3 3.8 300.0 7.9 127.50.66 0.34 Ex. (225) Com. (2-77) 5.3 3.8 300.0 8.0 125.3 0.66 0.34 Ex.(226) Com. (2-78) 5.3 3.9 300.0 7.6 127.6 0.66 0.34 Ex. (227) Com.(2-79) 5.2 3.8 300.0 7.8 128.4 0.66 0.34 Ex. (228) Com. (2-80) 5.4 3.7300.0 8.1 127.5 0.66 0.34 Ex. (229) Com. (2-81) 5.3 3.4 300.0 8.7 134.50.66 0.33 Ex. (230) Com. (2-82) 5.3 3.6 300.0 8.4 125.0 0.66 0.34 Ex.(231) Com. (2-83) 5.2 3.5 300.0 8.6 138.9 0.66 0.33 Ex. (232) Com.(2-84) 5.4 3.8 300.0 8.0 125.1 0.66 0.33 Ex. (233) Com. (2-85) 5.4 3.7300.0 8.1 128.0 0.66 0.33 Ex. (234) Com. (2-86) 5.5 3.7 300.0 8.1 126.60.66 0.33 Ex. (235) Com. (2-87) 5.4 3.7 300.0 8.1 128.1 0.66 0.33 Ex.(236) Com. (2-88) 5.5 3.6 300.0 8.3 128.4 0.66 0.34 Ex. (237) Com.(2-89) 5.5 3.6 300.0 8.4 128.2 0.66 0.33 Ex. (238) Com. (2-90) 5.4 3.6300.0 8.3 127.6 0.66 0.33 Ex. (239) Com. (2-91) 5.4 4.0 300.0 7.5 123.60.66 0.33 Ex. (240) Com. (2-92) 5.5 3.8 300.0 7.9 126.8 0.66 0.34 Ex.(241) Com. (2-93) 5.3 3.5 300.0 8.6 140.0 0.66 0.33 Ex. (242) Com.(2-94) 5.2 3.5 300.0 8.5 128.5 0.66 0.33 Ex. (243) Com. (2-95) 5.3 3.5300.0 8.5 132.5 0.66 0.34 Ex. (244) Com. (2-96) 5.3 3.6 300.0 8.3 128.00.66 0.34 Ex. (245) Com. (2-97) 5.4 3.7 300.0 8.2 124.6 0.66 0.33 Ex.(246) Com. (2-98) 5.4 3.8 300.0 7.9 124.1 0.66 0.33 Ex. (247) Com.(2-99) 5.4 3.7 300.0 8.1 123.9 0.66 0.34 Ex. (248) Com. (2-100) 5.4 3.7300.0 8.2 125.2 0.66 0.33 Ex. (249) Com. (2-101) 5.4 3.6 300.0 8.4 125.90.66 0.33 Ex. (250) Com. (2-102) 5.4 3.6 300.0 8.3 125.1 0.66 0.33 Ex.(251) Com. (2-103) 5.4 3.9 300.0 7.6 125.8 0.66 0.34 Ex. (252) Com.(2-104) 5.4 4.0 300.0 7.5 124.6 0.66 0.33 Ex. (253) Com. (2-105) 5.3 3.5300.0 8.6 127.1 0.66 0.33 Ex. (254) Com. (2-106) 5.3 3.5 300.0 8.6 127.10.66 0.33 Ex. (255) Com. (2-107) 5.3 3.7 300.0 8.2 126.4 0.66 0.33 Ex.(256) Com. (2-108) 5.3 3.5 300.0 8.6 127.7 0.66 0.34 Ex. (257) Com.(2-109) 5.2 3.6 300.0 8.3 124.3 0.66 0.34 Ex. (258) Com. (2-110) 5.3 3.5300.0 8.5 127.1 0.66 0.33 Ex. (259) Com. (2-111) 5.3 3.4 300.0 8.8 129.30.66 0.34 Ex. (260) Com. (2-112) 5.2 3.4 300.0 8.8 135.0 0.66 0.34 Ex.(261) Com. (2-113) 5.3 3.5 300.0 8.6 126.3 0.66 0.34 Ex. (262) Com.(2-114) 5.2 3.4 300.0 8.7 124.9 0.66 0.34 Ex. (263) Com. (2-115) 5.3 3.5300.0 8.5 127.3 0.66 0.33 Ex. (264) Com. (2-116) 5.5 3.6 300.0 8.3 128.30.66 0.34 Ex. (265) Com. (2-117) 5.5 3.6 300.0 8.3 125.3 0.66 0.33 Ex.(266) Com. (2-118) 5.3 3.5 300.0 8.5 128.5 0.66 0.34 Ex. (267) Com.(2-119) 5.5 4.0 300.0 7.5 124.8 0.66 0.34 Ex. (268) Com. (2-120) 5.5 3.9300.0 7.7 128.6 0.66 0.34

It can be seen from the results in Table 4 above that the compounds ofcomparative examples 1 to 7 exhibited a lower driving voltage, lowerefficiency, and a lower lifespan than the inventive compounds.

Especially, Comparative Examples 2 to 7 have similar biscarbazole typesto the inventive compounds, but produce different results depending onthe presence or absence and location of a ring on the carbazolebackbone.

It can be confirmed that Comparative Examples 2 and 7, in which a ringis not formed on the carbazole backbone, exhibited the highest drivingvoltage, lowest efficiency, and lowest lifespan among the comparativeexamples, and Comparative Examples 3 to 6, in which a ring is formed onthe outside phenyl of the carbazole backbone, exhibited a lower drivingvoltage and relatively higher efficiency and lifespan than ComparativeExamples 2 and 7.

However, the inventive compounds, in which a ring is formed on thebackbone connecting two carbazole moieties, exhibited very excellentefficiency and lifespan characteristics and lower or similar drivingvoltages compared with Comparative Examples 3 to 6.

The reason is that, the compound in which a ring is present on thebackbone connecting two carbazole moieties has a deeper HOMO energylevel compared with the compound in which a ring is formed on theoutside portion of the carbazole backbone, and thus holes overflow tothe light emitting layer more promptly to increase the lifespan, and thelight emission occurs inside the light emitting layer but not at thelight emitting layer-hole transport layer interface, thereby achievinghigher efficiency.

Although exemplary embodiments of the present invention have beendescribed for illustrative purposes, a person skilled in the art willappreciate that various modifications, additions and substitutions arepossible, without departing from the scope and spirit of the inventionas disclosed in the accompanying claims. Therefore, the embodimentdisclosed in the present invention is intended to illustrate the scopeof the technical idea of the present invention, and the scope of thepresent invention is not limited by the embodiment. The scope of thepresent invention shall be construed on the basis of the accompanyingclaims, and it shall be construed that all of the technical ideasincluded within the scope equivalent to the claims belong to the presentinvention.

EXPLANATION OF NUMERICAL REFERENCES

100: organic electronic device 110: substrate.

120: First electrode 130: hole injection layer.

140: hole transport layer 141: buffer layer.

150: light emitting layer 151: emission-auxiliary layer.

160: electron transport layer 170: electron injection layer.

180: cathode.

What is claimed is:
 1. A compound represented by Formula 4:

wherein in Formula 4, (1) L is a C₂˜C₂₀ heterocyclic group containing atleast one heteroatom of O, N, S, Si, and P; (2) Ar₁ and Ar₂ are eachindependently selected from the group consisting of a fluorenyl group; asilane group; a C₆˜C₆₀ aryl group; a C₂˜C₂₀ alkenyl group; a C₂˜C₆₀heterocyclic group containing at least one heteroatom of O, N, S, Si,and P; a C₁˜C₅₀ alkyl group; and a fused cyclic group of a C₆˜C₆₀aromatic ring and a C₃˜C₆₀ aliphatic ring; (3) X₁ to X₄ are eachindependently CR′ or N; and (4) R′ is selected from the group consistingof hydrogen; a C₆˜C₆₀ aryl group; a fluorenyl group; a C₂˜C₆₀heterocyclic group containing at least one heteroatom of O, N, S, Si,and P; a C₁˜C₅₀ alkyl group; and a fused cyclic group of a C₆˜C₆₀aromatic ring and a C₃˜C₆₀ aliphatic ring; and a C₂˜C₂₀ alkenyl group.2. An organic electronic element comprising a first electrode, a secondelectrode, and an organic material layer disposed between the firstelectrode and the second electrode, wherein the organic material layercontains the compound of claim
 1. 3. The organic electronic element ofclaim 2, wherein the organic material layer is formed by a solubleprocess using the compound.
 4. The organic electronic element of claim2, wherein the organic material layer includes at least one of a lightemitting layer, a hole injection layer, a hole transport layer, anelectron injection layer, an electron transport layer, and anemission-auxiliary layer.
 5. The organic electronic element of claim 3,wherein the compound is used as a host material for a light emittinglayer.
 6. An electronic device, comprising: a display device includingthe organic electronic element of claim 3; and a controller driving thedisplay device.
 7. The electronic device of claim 6, wherein the organicelectronic element is at least one of an organic light emitting diode,an organic solar cell, an organic solar cell, an organic photoconductor, an organic transistor, and an element for a monochromatic orwhite lighting.